Pyrone-3-carboxamide compounds and herbicidal composition thereof

ABSTRACT

A compound of the formula (I) ##STR1## wherein (1) when R 1  is a C 2-11  alkyl, a lower alkenyl, a lower alkynyl, a cycloalkyl, a lower alkoxyalkyl, an aralkyl which may be substituted, a lower haloalkyl or a 5 or 6 membered heterocycle; 
     R 2 , R 3  and R 4  are the same or different, hydrogen, a halogen, cyano, nitro, amino, a lower alkyl, a lower haloalkyl, hydroxy, a lower alkoxy, an aryloxy, carboxy, or a lower alkoxycarbonyl; 
     R 5  is hydrogen, a halogen, a C 1-11  alkyl, an aryl which may be substituted, an aralkyl which may be substituted; 
     R 6  is a C 1-11  alkyl, a lower alkenyl, a lower alkynyl, a cycloalkyl, a lower alkoxyalkyl, an aryl which may be substituted, an aralkyl which may be substituted, a lower haloalkyl, or a 5 or 6 membered heterocycle; or R 5  and R 6  may be combined to form a group of --(CH 2 ) m  -- (m is 3 or 4); 
     (2) when R 1  is an aryl which may be substituted; 
     R 2 , R 3 , R 4  and R 5  have the same meanings as defined above; R 6  is a C 1-11  alkyl, a lower alkenyl, a lower alkynyl, a cycloalkyl, a lower alkoxyalkyl, an aralkyl which may be substituted, a haloalkyl or a 5 or 6 membered heterocycle, or R 5  and R 6  may be combined to form a group of --(CH 2 ) m  -- (m is 3 or 4); 
     (3) when R 1  is methyl; 
     R 2 , R 3 , R 4  and R 5  have the same meanings as defined above; R 6  is a C 2-12  alkyl, a lower alkenyl, a lower alkynyl, a cycloalkyl, a lower alkoxyalkyl, an aryl which may be substituted, an aralkyl which may be substituted, a lower haloalkyl or a 5 or 6 membered heterocycle or R 5  and R 6  may be combined to form a group of --(CH 2 ) m  -- (m is 3 or 4); or 
     (4) when R 1  and R 6  are methyl; 
     R 2 , R 3  and R 4  have the same meanings as defined above; R 5  is a halogen, a C 1-11  alkyl, an aryl which may be substituted or an aralkyl which may be substituted, which is useful as herbicide.

BACKGROUND OF THE INVENTION

1. Field of the Invention

This invention relates to novel pyrone-3-carboxamide compounds andherbicidal compositions thereof, and to novel growth regulating agents.

2. Description of the Prior Art

Certain compounds belonging to 4-oxo-4H-pyran-3-carboxamides have beenmentioned in the literature.

That is, it has been known that the treatment of o-haloacetoanilides(2-chloro, 2-bromo, 2,4-dichloro or 2,5-dichloro compound) withpolyphosphoric acid for an hour at 140° C. gives the correspondinghalogen derivatives of2,6-dimethyl-4-oxo-N-phenyl-4H-pyran-3-carboxamide (A. K. Mallams and S.S. Islaelstam: J. Org. Chem., 29, 3548 (1964); A. K. Mallams: J. Org.Chem., 29, 3555 (1964)). This method using polyphosphoric acid wasapplied on other acetoacetoanilides (2-fluoro, 2-piperidino,2-hexahydroazepinyl, 2-morpholino, 2-pyrrolidinyl or the like) orbenzoylacetoanilides to yield the corresponding4-oxo-4H-pyran-3-carboxamide compounds [R. Garner and H. Suschitzky: J.Chem. Soc. (C), 186 (1966)].

Also, 4-oxo-N-2,6-triphenyl-4H-pyran-3-carboxamide was obtained bytreating benzoylacetoanilide with succinyl dichloride[Zankowska-Jasinsca. W. et al.: Zesz. Nawk. Uniw. Jagiellon., Pr. Chem.1980, 25, 7; ibid 1976, 21, 141].

The formation of2,6-dimethyl-N-(4-nitrophenyl)-4-oxo-4H-pyran-3-carboxamide wasidentified as the reaction product between p-nitroaniline and diketene[(Kato and Kubota; Yakugakuzassi, 87, 1212 (1967)]. Also,N-(2-chlorophenyl)-2,6-dimethyl-4-oxo-4H-pyran-3-carboxamide wasobtained by treating 2,6-dimethyl-4-oxo-4H-pyran-3-carboxylic acid withthionyl chloride followed by the reaction with o-chloroaniline, or byheating p-nitrophenyl ester of 2,6-dimethyl-4-oxo-4H-pyran-3-carboxylicacid and o-chloroaniline for 4.3 hours at 110° C. [Toda: Yakugakuzassi,87, 1351 (1967)]. This literature disclosed pyrone-3-carboxamidecompounds which were obtained by the reaction of 2-aminotroponesor4-aminotropolones with diketene.

Also, in Japanese Patent Publication No. 45(1970)-31663, it disclosed aprocess for preparing 2,6-dimethyl-4-oxo-4H-pyran-3-carboxamides whichcomprises reacting isocyanates and diketene in the presence of an acidcatalyst, and specifically disclosed in the working examples2,6-dimethyl-4-oxo-N-phenyl-4H-pyran-3-carboxamide,2,6-dimethyl-N-(2-methylphenyl)-4-oxo-4H-pyran-3-carboxamide,N-(2-chlorophenyl)-2,6-dimethyl-4-oxo-4H-pyran-3-carboxamide,2,6-dimethyl-N-(2-nitrophenyl)-4-oxo-4H-pyran-3-carboxamide,N-(2,5-dichlorophenyl)-2,6-dimethyl-4-oxo-4H-pyran-3-carboxamide,2,6-dimethyl-N-(3-nitrophenyl)-4-oxo-4H-pyran-3-carboxamide and2,6-dimethyl-N-(4-methylphenyl)-4-oxo-4H-pyran-3-carboxamide.

Further, 2,6-dimethyl-4-oxo-N-phenyl-4H-pyran-3-carboxamide,N-(4-methoxyphenyl)-2,6-dimethyl-4-oxo-4H-pyran-3-carboxamide andN-(4-chlorophenyl)-2,6-dimethyl-4-oxo-4H-pyran-3-carboxamide have beendisclosed as the reaction products between 3-morpholinocrotonanilidecompounds and diketene [Kato et al: Yakugakuzassi, 101, 43 (1981)].

In addition, there have been reports about pyrone-3-carboxamidecompounds which correspond to aminotropones [H. Toda and S. Seto: Chem.Pharm. Bull., 19, 1477 (1971)], aminopyridines [T. Kato et al: Chem.Pharm. Bull., 20, 133 (1972); ibid. 28, 2129 (1980); H. L. Yale et al:J. Heterocyclic Chem., 14, 637 (1977)] and 2-amino-1,3,4-thiadiazoles[R. F. Lauer et al: J. Heterocyclic Chem., 13, 291 (1976)],respectively.

It was disclosed in the above mentioned Japanese Patent Publication No.45(1970)-31663 that 2,6-dimethyl-4-oxo-4H-pyran-3-carboxamides haveutility as agricultural drugs such as a control agent of sheath blightof rice, nematicide or acaricide, or drugs such as an antiviral agent orthe like, but did not disclose any data supporting such utility.

There have been no reports on the pyrone-3-carboxamide compoundsrepresented by the formula (I) of the present invention (set forthbelow), nor has there been any suggestion regarding possible plantgrowth inhibitory activity.

SUMMARY OF THE INVENTION

This invention provides compounds of the formula (I). ##STR2##

In the formula (I),

(1) when

R₁ is a C₂₋₁₁ alkyl, a lower alkenyl, a lower alkynyl, a cycloalkyl, alower alkoxyalkyl, an aralkyl which may be substituted, a lowerhaloalkyl or a 5 or 6 membered heterocycle;

R₂, R₃ and R₄ are the same or different, hydrogen, a halogen, cyano,nitro, amino, a lower alkyl, a lower haloalkyl, hydroxy, a lower alkoxy,an aryloxy, carboxy, or a lower alkoxycarbonyl;

R₅ is hydrogen, a halogen, a C₁₋₁₁ alkyl, an aryl which may besubstituted, an aralkyl which may be substituted;

R₆ is a C₁₋₁₁ alkyl, a lower alkenyl, a lower alkynyl, a cycloalkyl, alower alkoxyalkyl, an aryl which may be substituted, an aralkyl whichmay be substituted, a lower haloalkyl, or a 5 or 6 membered heterocycle;or R₅ and R₆ may be combined to form a group of --(CH₂)_(m) -- (m is 3or 4);

(2) when

R₁ is an aryl which may be substituted;

R₂, R₃, R₄ and R₅ have the same meanings as defined above; R₆ is a C₁₋₁₁alkyl, a lower alkenyl, a lower alkynyl, a cycloalkyl, a loweralkoxyalkyl, an aralkyl which may be substituted, a haloalkyl or a 5 or6 membered heterocycle, or R₅ and R₆ may be combined to form a group of--(CH₂)_(m) -- (m is 3 or 4);

(3) when

R₁ is methyl;

R₂, R₃, R₄ and R₅ have the same meanings as defined above; R₆ is a C₂₋₁₂alkyl, a lower alkenyl, a lower alkynyl, a cycloalkyl, a loweralkoxyalkyl, an aryl which may be substituted, an aralkyl which may besubstituted, a lower haloalkyl or a 5 or 6 membered heterocycle or R₅and R₆ may be combined to form a group of --(CH₂)_(m) -- (m is 3 or 4);or

(4) when

R₁ and R₆ are methyl;

R₂, R₃ and R₄ have the same meanings as defined above; R₅ is a halogen,a C₁₋₁₁ alkyl, an aryl which may be substituted or an aralkyl which maybe substituted.

Also, the invention provides a herbicidal composition which comprises acompound of the above mentioned formula (I) as the active ingredient.

DESCRIPTION OF PREFERRED EMBODIMENTS

The term "lower" which is used to describe the lower alkyl, lower alkoxyor like group in this invention means a group containing 1-5 carbonatoms. Specifically, the lower alkyl group may be methyl, ethyl, propyl,isopropyl, butyl, isobutyl, pentyl or isopentyl; the lower alkoxy groupmay be methoxy, ethoxy, propoxy, isopropoxy or butoxy; the loweralkoxycarbonyl group may be methoxycarbonyl, ethoxycarbonyl,propoxycarbonyl or butoxycarbonyl; the lower alkenyl or lower alkynylgroup may be vinyl, allyl, isopropenyl 2-butenyl, 1,3-butadienyl,2-pentenyl, 1,4-pentadienyl, 1,6-heptadienyl, 1-hexenyl, ethynyl or2-propynyl.

Examples of the cycloalkyl groups include cyclopropyl, cyclopentyl orcyclohexyl.

Examples of the lower halolakyl groups include trifluoromethyl orchloromethyl.

Examples of the lower alkoxyalkyl groups include methoxymethyl,ethoxymethyl, propoxymethyl or butoxymethyl.

Examples of the lower alkoxycarbonyl group include methoxycarbonyl,ethoxycarbonyl or propoxycarbonyl.

Examples of the halogen atom include chlorine, bromine, fluorine oriodine.

Examples of the aryl in the aryl group which may be substituted includephenyl or naphthyl.

Examples of the aralkyl in the aralkyl group which may be substitutedinclude benzyl, 3-phenylpropyl, 4-phenylbutyl.

Examples of the aryloxy groups include phenyloxy or naphthyloxy.

The 5- or 6-membered heterocyclic group means a 5- or 6-membered groupcontaining one to three hetero atoms selected from nitrogen atom, oxygenatom and sulfur atom. Examples of the 5-membered heterocyclic groups arefuryl, tetrahydrofuryl, thienyl, thiazolyl, isothiazolyl, oxazolyl,isooxazolyl or pyrazolyl and the 6-membered heterocyclic groups arepyridyl, pyrimidinyl, pyrazinyl or pyridazinyl. These heterocyclicgroups may be substituted by alkyl as methyl or ethyl, halogen atom orphenyl. When the heterocyclic group is substituted by phenyl, it mayform a condensed ring combining the two adjacent carbon atoms in theheterocyclic group with phenyl group. Examples of the condensed ring arebenzothiazolyl, benzofuryl, quinazolinyl or quinoxalinyl group.

Examples of substituents on the aryl or aralkyl group which may besubstituted include a halogen, a lower alkyl, a lower alkoxy or cyanoand numbers of the substituents are preferred to be one to three.

The compound of the formula (I) in this invention may form an additionsalt with an acid such as hydrochloric acid, sulfuric acid, phosphoricacid, methanesulfonic acid, p-toluenesulfonic acid or trifluoroaceticacid when sufficiently basic, and also form a salt with an inorganicbase when it contains a carboxyl group. Such salts are also included inthis invention.

The compound of the formula (I) in this invention may be prepared by anyof the following methods. ##STR3## [R₁, R₂, R₃, R₄ and R₅ of the formula(II) and (II') are the same as those in the formula (I), R₇ is adialkylamino and n is an integer from 0 to 6.]

This method comprises reacting a compound of the general formula (II) or(II') with diketene in an appropriate solvent (e.g., toluene or xylene)at a temperature of e.g., -20° C.˜130° C. This method is suitable toobtain a compound in which R₅ is hydrogen and R₆ is methyl.

The compounds (II) and (II') which may be used as the starting materialof the above reaction can be easily prepared by condensing a β-ketoamidederivative of the general formula: ##STR4## with an amine of the generalformula: R₇ (CH₂)_(n) NH₂, wherein the symbols have the same meanings asdefined above. ##STR5## [R₁, R₂, R₃ and R₄ have the same meanings asthose in the general formula (I), R₈ is an alkyl, cycloalkyl, aryl orheterocyclic group.]

This method comprises reacting a compound of the general formula (III)with diketene in the presence of a tertiary base in an appropriatesolvent (e.g., toluene or xylene) at a temperature -20° C.˜130° C. Thismethod is suitable to obtain a compound in which R₅ is hydrogen and R₆is methyl.

The compound (III) as the starting material in the above reaction can beeasily obtained by condensing a β-ketoamide derivative of the generalformula: ##STR6## with an amine of the general formula: R₈ NH₂, whereinthe symbols are the same as defined above. ##STR7## R₁, R₂, R₃, R₄, R₅,R₆, R₇ and n are the same as those in the general formulae (I) and (II),R₉ and R₁₀ are hydrogen, an alkyl or phenyl, or when both R₉ and R₁₀ arealkyl, they may be combined to form a cycloalkyl.

This method comprises reacting a compound of the general formula (II) or(II') with a compound of the general formula (IV), in the presence orabsence of an appropriate solvent (e.g., toluene, benzene or mesitylene)under heating (e.g., at 100° to 170° C.).

The compounds (IV) of the starting material in the above reaction can beprepared by a known method e.g., Chem. Pharm. Bull. 31, 1896 (1983);Japanese Unexamined Patent Publication Nos. 106478/1979 and 22077/1986.##STR8## R₁, R₂, R₃, R₄, R₅, R₆, R₈, R₉ and R₁₀ have the same meaningsas defined above.

This method comprises reacting a compound of the general formula (III)with a compound of the general formula (IV) in the presence or absenceof a tertiary base in the presence or absence of an appropriate solvent(e.g., toluene, benzene or mesitylene) under heating (e.g., at 100°˜170°C.). ##STR9## [R₁, R₂, R₃, R₄, R₅, R₆, R₇ and n have the same meaningsas defined above and R₁₁ is alkyl group.]

This method comprises reacting a compound of the general formula (II) or(II') with a compound of the general formula (V) in the presence ofmolecular sieve, in an inert solvent (e.g., xylene or mesitylene) underheating.

The compounds (I) of this invention are useful as a herbicide for apaddy field, vegetable field (field farm), fruit garden, meadow, lawn,woods and other fields of grass.

For herbicidal applications, the compounds of the present invention aregenerally formulated into herbicidal compositions. These compositionscan be solids such as dusts, granules, or wettable powders; or they canbe liquids such as solutions, aerosols, or emulsifiable concentrates.

For example, solid compositions such as dusts, wettable powders orgranules can be prepared by blending the active compound with a solidinert carrier such as the kaolinites, bentonites, clays, talcs, silicasand the like. Liquids compositions such as solutions or emulsifiableconcentrates can be prepared by dissolving the active compound with aliquid inert solvent such as xylene, ethanol, acetone,dimethylformamide, some vegetable oils, water and so on.

Surface active agents for wetting, dispersing or emulsifying aregenerally used with the herbicidal compositions as above defined. Forexample, polyoxyethylene-alkyl ethers, polyoxyethylene-sorbitan fattyacid esters, and other nonionic types; alkyl and alkylarlyl sulfonatesand sulfates and their sodium salts and other anionic types or othertypes of surface active agents may be employed.

For pre-emergence applications these herbicidal compositions are usuallyapplied either as sprays, dusts, or granules in the area in whichsuppression of vegetation is desired. For post-emergence applicationscontrol of established plant growth, sprays or dusts are most commonlyused. These formulations may contain 10-80% for wettable powders, 1-10%for granules, or 10-50% for emulsifiable concentrates by weight ofactive ingredient. Dosage of these herbicidal compositions forpre-emergence or post-emergence applications is generally 0.1-2 Kg byweight of active ingredient, per acre.

This invention is illustrated further by examples hereinafter. Also,growth-regulating activities on plants of the compounds of the inventionare shown in reference examples.

Furthermore, related specific compounds in addition to the compoundsshown in the examples are as follows;

N-(4-bromo-2,6-diethylphenyl)-6-methyl-4-oxo-2-phenyl-4H-pyran-3-carboxamide,

N-(4-chloro-2,6-diethylphenyl)-6-methyl-4-oxo-2-phenyl-4H-pyran-3-carboxamide,

2-butyl-N-(4-chloro-2,6-diethylphenyl)-6-methyl-4-oxo-4H-pyran-3-carboxamide,

2-butyl-N-(4-chloro-2,6-diethylphenyl)-5,6-dimethyl-4-oxo-4H-pyran-3-carboxamide,

2-(3-cyanophenyl)-6-methyl-4-oxo-N-phenyl-4H-pyran-3-carboxamide,

2-(3-methoxyphenyl)-6-methyl-4-oxo-N-phenyl-4H-pyran-3-carboxamide,

5-bromo-N-(2,6-diethylphenyl)-6-methyl-4-oxo-2-propyl-4H-pyran-3-carboxamide,

5-bromo-2-butyl-N-(2,6-diethylphenyl)-6-methyl-4-oxo-4H-pyran-3-carboxamide

5-bromo-N-(4-bromo-2,6-diethylphenyl)-6-methyl-4-oxo-2-propyl-4H-pyran-3-carboxamide,

5-bromo-N-(4-bromo-2,6-diethylphenyl)-2-butyl-6-methyl-4-oxo-4H-pyran-3-carboxamide,

5-chloro-N-(2,6-diethylphenyl)-6-methyl-4-oxo-2-propyl-4H-pyran-3-carboxamide,

2-butyl-5-chloro-N-(2,6-diethylphenyl)-6-methyl-4-oxo-4H-pyran-3-carboxamide,

5-chloro-N-(4-chloro-2,6-diethylphenyl)-6-methyl-4-oxo-2-propyl-4H-pyran-3-carboxamide,

2-butyl-5-chloro-N-(4-chloro-2,6-diethylphenyl)-6-methyl-4-oxo-4H-pyran-3-carboxamide,

N-(4-bromo-2,6-diethylphenyl)-5-chloro-6-methyl-4-oxo-2-propyl-4H-pyran-3-carboxamide,

N-(4-bromo-2,6-diethylphenyl)-2-butyl-5-chloro-6-methyl-4-oxo-4H-pyran-3-carboxamide,

5-bromo-N-(4-chloro-2,6-diethylphenyl)-6-methyl-4-oxo-2-propyl-4H-pyran-3-carboxamide,

5-bromo-2-butyl-N-(4-chloro-2,6-diethylphenyl)-6-methyl-4-oxo-4H-pyran-3-carboxamide,

2-(3-trifluoromethylphenyl)-N-(2,4-difluorophenyl)-6-methyl-4-oxo-4H-pyran-3-carboxamide,

2-(3-bromophenyl)-N-(2,4-difluorophenyl)-6-methyl-4-oxo-4H-pyran-3-carboxamide,

N-(2,4-difluorophenyl)-6-methyl-2-(3-nitrophenyl)-4-oxo-4H-pyran-3-carboxamide,

2-ethoxymethyl-N-(2,6-diethylphenyl)-6-methyl-4-oxo-4H-pyran-3-carboxamide,

2-ethoxymethyl-N-(2,6-diethylphenyl)-5,6-dimethyl-4-oxo-4H-pyran-3-carboxamide,

N-(4-bromo-2,6-diethylphenyl)-2-ethoxymethyl-6-methyl-4-oxo-4H-pyran-3-carboxamide,

N-(4-bromo-2,6-diethylphenyl)-2-ethoxymethyl-5,6-dimethyl-4-oxo-4H-pyran-3-carboxamide,

N-(2,6-diethylphenyl)-6-methyl-4-oxo-2-propoxymethyl-4H-pyran-3-carboxamide

N-(2,6-diethylphenyl)-5,6-dimethyl-4-oxo-2-propoxymethyl-4H-pyran-3-carboxamide,

N-(4-bromo-2,6-diethylphenyl)-6-methyl-4-oxo-2-propoxymethyl-4H-pyran-3-carboxamide,

N-(4-bromo-2,6-diethylphenyl)-5,6-dimethyl-4-oxo-2-propoxymethyl-4H-pyran-3-carboxamide,

2-(2-ethoxyethyl)-N-(2,6-diethylphenyl)-6-methyl-4-oxo-4H-pyran-3-carboxamide,

2-(2-ethoxyethyl)-N-(2,6-diethylphenyl)-5,6-dimethyl-4-oxo-4H-pyran-3-carboxamide,

2-(2-ethoxyethyl)-N-(2,6-diethylphenyl)-5,6-dimehtyl-4-oxo-4H-pyran-3-carboxamide,

N-(4-bromo-2,6-diethylphenyl)-2-(2-ethoxyethyl)-6-methyl-4-oxo-4H-pyran-3-carboxamide,

N-(4-bromo-2,6-diethylphenyl)-2-(2-ethoxyethyl)-5,6-dimethyl-4-oxo-4H-pyran-3-carboxamide,

5-bromo-N-(2,6-diethylphenyl)-2-methoxymethyl-6-methyl-4-oxo-4H-pyran-3-carboxamide,

5-bromo-N-(4-bromo-2,6-diethylphenyl)-2-methoxymethyl-6-methyl-4-oxo-4H-pyran-3-carboxamide,

5-bromo-N-(2,6-diethylphenyl)-6-methyl-4-oxo-2-propoxymethyl-4H-pyran-3-carboxamide,

5-bromo-N-(4-bromo-2,6-diethylphenyl)-6-methyl-4-oxo-2-propoxymethyl-4H-pyran-3-carboxamide

5-bromo-2-(2-ethoxyethyl)-N-(2,6-diethylphenyl)-6-methyl-4-oxo-4H-pyran-3-carboxamide,

5-bromo-N-(2,6-diethylphenyl)-2-methoxymethyl-6-methyl-4-oxo-4H-pyran-3-carboxamide,

5-bromo-N-(4-bromo-2,6-diethylphenyl)-2-(2-ethoxyethyl)-6-methyl-4-oxo-4H-pyran-3-carboxamide,

N-(4-bromo-2,6-diethylphenyl)-5-chloro-2-methoxymethyl-6-methyl-4-oxo-4H-pyran-3-carboxamide,

5-chloro-N-(2,6-diethylphenyl)-6-methyl-4-oxo-2-propoxymethyl-4H-pyran-3-carboxamide,

N-(4-bromo-2,6-diethylphenyl)-5-chloro-6-methyl-4-oxo-2-propoxymethyl-4H-pyran-3-carboxamide,

5-chloro-2-(2-ethoxyethyl)-N-(2,6-diethylphenyl)-6-methyl-4-oxo-4H-pyran-3-carboxamide,

N-(4-bromo-2,6-diethylphenyl)-5-chloro-2-(2-ethoxyethyl)-6-methyl-4-oxo-4H-pyran-3-carboxamide,

5-bromo-N-(4-bromo-2,6-diethylphenyl)-2-ethoxymethyl-6-methyl-4-oxo-4H-pyran-3-carboxamide,

5-bromo-2-ethoxymethyl-N-(2,6-diethylphenyl)-6-methyl-4-oxo-4H-pyran-3-carboxamide,

N-(4-bromo-2,6-diethylphenyl)-5-chloro-2-ethoxymethyl-6-methyl-4-oxo-4H-pyran-3-carboxamide,

5-chloro-2-ethoxymethyl-N-(2,6-diethylphenyl)-6-methyl-4-oxo-4H-pyran-3-carboxamide,

5-dodecyl-N-(2,6-diethylphenyl)-6-methyl-4-oxo-2-propyl-4H-pyran-3-carboxamide,

2-ethyl-4-oxo-N-phenyl-6-(3-pyridyl)-4H-pyran-3-carboxamide,

N-(2,6-diethyl-4-trifluoromethylphenyl)-5,6-dimethyl-4-oxo-2-propyl-4H-pyran-3-carboxamide,

5-bromo-N-(4-cyanophenyl)-4-oxo-2-phenyl-6-propyl-4H-pyran-3-carboxamide,

2-(3-chlorophenyl)-5-ethyl-6-hexyl-N-(3-nitrophenyl)-4-oxo-4H-pyran-3-carboxamide,

N-(4-aminophenyl)-5-hexyl-6-nonyl-4-oxo-2-phenyl-4H-pyran-3-carboxamide,

6-dodecyl-N-(4-hydroxyphenyl)-5-nonyl-4-oxo-2-phenyl-4H-pyran-3-carboxamide

6-allyl-5-dodecyl-N-(2,6-diethyl-4-methoxyphenyl)-4-oxo-2-phenyl-4H-pyran-3-carboxamide,

4-oxo-N-(4-phenoxyphenyl)-5,6-diphenyl-6-(2-propynyl)-4H-pyran-3-carboxamide,

N-(2-carboxyphenyl)-6-cyclopropyl-4-oxo-2-phenyl-5-phenylmethyl-4H-pyran-3-carboxamide,

N-(2-methoxycarbonylphenyl)-6-methoxymethyl-4-oxo-2-phenyl-4H-pyran-3-carboxamide,

N-(2,6-diethylphenyl)-4-oxo-2,5-diphenyl-6-phenylmethyl-4H-pyran-3-carboxamide,

N-(2,6-diethylphenyl)-4-oxo-2-phenyl-6-trifluoromethyl-4H-pyran-3-carboxamide,

5,6,7,8-tetrahydro-4-oxo-N-2-diphenyl-4H-benzopyran-3-carboxamide,

5-bromo-N-(4-cyano-2,6-diethylphenyl)-2-methyl-4-oxo-6-propyl-6-propyl-4H-pyran-3-carboxamide,

5-ethyl-6-heptyl-N-(4-nitrophenyl)-2-methyl-4-oxo-4H-pyran-3-carboxamide,

N-(4-aminophenyl)-6-dodecyl-2-methyl-4-oxo-5-pentyl-4H-pyran-3-carboxamide,

6-allyl-2-methyl-5-octyl-4-oxo-N-(4-trifluoromethylphenyl)-4H-pyran-3-carboxamide,

5-dodecyl-N-(4-hydroxyphenyl)-2-methyl-4-oxo-6-(2-propynyl)-4H-pyran-3-carboxamide,

6-cyclohexyl-2-methyl-N-(4-methoxyphenyl)-4-oxo-5-phenyl-4H-pyran-3-carboxamide,

6-butyl-2-methyl-4-oxo-N-(4-phenoxyphenyl)-5-phenylmethyl-4H-pyran-3-carboxamide,

5-chloro-N-(4-ethoxycarbonyl-2,6-diethylphenyl)-2-methyl-4-oxo-6-phenylmethyl-4H-pyran-3-carboxamide,

N-(4-carboxyphenyl)-2-methyl-5-(2-methylpropyl)-4-oxo-6-(3-pyridyl)-4H-pyran-3-carboxamide,

5-bromo-2,6-dimethyl-4-oxo-N-phenyl-4H-pyran-3-carboxamide,

5-chloro-N-(4-cyanophenyl)-2,6-dimethyl-4-oxo-4H-pyran-3-carboxamide,

N-(4-amino-2,6-diethylphenyl)-5-hexyl-2,6-dimethyl-4-oxo-4H-pyran-3-carboxamide,

N-(2,6-diethyl-4-trifluoromethylphenyl)-2,6-dimethyl-5-nonyl-4-oxo-4H-pyran-3-carboxamide,

5-dodecyl-N-(2,6-diethyl-4-hydroxyphenyl)-2,6-dimethyl-4-oxo-4H-pyran-3-carboxamide,

N-(4-ethoxy-2,6-diethylphenyl)-2,6-dimethyl-4-oxo-5-phenyl-4H-pyran-3-carboxamide,

2,6-dimethyl-4-oxo-N-(4-phenoxyphenyl)-5-(3-trifluoromethylphenyl)-4H-pyran-3-carboxamide,

N-(2,6-diethyl-4-nitrophenyl)-2,5,6-trimethyl-4-oxo-4H-pyran-3-carboxamide,

N-(4-carboxy-2,6-diethylphenyl)-2,5,6-trimethyl-4-oxo-4H-pyran-3-carboxamide,

N-(2,6-diethyl-4-methoxycarbonylphenyl)-2,5,6-trimethyl-4-oxo-4H-pyran-3-carboxamide,

6-methoxymethyl-4-oxo-N-phenyl-2-propyl-4H-pyran-3-carboxamide and

6-methoxymethyl-4-oxo-N-2-diphenyl-4H-pyran-3-carboxamide.

The following Table 1 and Table 2 show physical properties of thecompounds of this invention. Table 3 shows "Evaluation" of therepresentative compounds of this invention.

EVALUATION TEST

A carrier was prepared by mixing 50 parts (by weight) of talc, 25 partsof bentonite, 2 parts of Solpole-9047 (Toho Chemical Co., Ltd, Japan)and 3 parts of Solpole-5039 (Toho Chemical Co., Ltd, Japan). 50 parts ofa test compound and 200 parts of the carrier were mixed to obtain 20%wettable powder, followed by dispersing the powder in distilled water tomake a dispersion of the defined concentrations.

Seeds of Oryza sativa L., Echinochloa crus-galli L., and Raphanussativus L. were germinated in a laboratory dish, to which the dispersionwas added. After breeding for 7 days in a thermostatic box kept at 25°C. under illumination of fluorescent tubes, growth of plant wasobserved. In the column of "Evaluation" of Table 3, the designation 1denotes no influence, 2 denotes 25% growth inhibition, 3 denotes 50%growth inhibition, 4 denotes 75% growth inhibition and 5 denotes 100%growth inhibition.

EXAMPLE 1 2-Ethyl-6-methyl-4-oxo-N-phenyl-4H-pyran-3-carboxamide(Compound No. 1)

A mixture of 1.91 g (10 m mol) of 3-oxo-N-phenyl-pentamide, 0.9 g (15 mmol) of N,N-dimethylhydrazine and 15 ml of toluene was stirred for 8hours at 60° C. and further heated at a more elevated temperature todistill off unreacted N,N-dimethylhydrazine and the resulted watertogether with about 10 ml of toluene. While refluxing the mixture, 2.10g (25 m mol) of diketene was dropwise added to it during 5 minutes, andthen heated under reflux for 2 hours. After cooling to room temperature,the precipitated crystals were separated by filtration, washed and driedto afford 0.900 g of the title compound (yield: 35%).

EXAMPLE 2 6-Methyl-4-oxo-N-phenyl-2-propyl-4H-pyran-3-carboxamide(Compound No. 2)

A mixture of 2.05 g (10 m mol) of 3-oxo-N-phenyl hexanamide (m.p.77.0°˜78.5° C.), 0.9 g (15 m mol) of N,N-dimethylhydrazine and 15 ml oftoluene was stirred for 8 hours at 60° C. and further heated to a moreelevated temperature to distill off the unreacted N,N-dimethylhydrazineand the resulted water together with about 2 ml of toluene. Whilerefluxing, to the mixture was dropwise added a solution of 3.90 g (25 mmol) of 2-ethyl-2,6-dimethyl-4H-1,3-dioxin-4-one in 8 ml of tolueneduring 30 minutes. While refluxing for 2.5 hours, 3 ml of toluene wasremoved. After cooling to room temperature, the precipitated crystalswere separated, washed and dried under vacuo to afford 1.32 g of thetitle compound (yield: 49%).

EXAMPLE 3N-(2,6-Diethylphenyl)-5,6-dimethyl-4-oxo-2-propyl-4H-pyran-3-carboxamide(Compound No. 3)

A mixture of 5.22 g (20 m mol) ofN-(2,6-diethylphenyl)-3-oxo-hexanamide, 2.40 g (40 m mol) ofN,N-dimethylhydrazine and 40 ml of toluene was stirred for 6 hours at60° C., and further heated to a more elevated temperature to distill offthe unreacted N,N-dimethylhydrazine and resulted water together withabout 12 ml of toluene. After the remaining solvent in the mixture wasremoved under vacuo by a rotary-evaporator, 6.27 g (44 m mol) of2,2,5,6-tetramethyl-4H-1,3-dioxin-4-one and 20 ml of mesitylene wereadded to the residue. While refluxing gently for 1.5 hours, the resultedacetone was removed. The solvent was removed under vacuo, and theresidue was subjected to silica gel column chromatography, and theresulted residue was crystallized to afford 5.39 g of the title compound(yield: 78.9%).

EXAMPLE 4N-(4-Chlorophenyl)-2-methyl-4-oxo-6-phenyl-4H-pyran-3-carboxamide(Compound No. 4)

A mixture of 2.12 g (10 m mol) of p-chloroacetoacetanilide, 1.07 g (10 mmol) of benzylamine and 20 ml of toluene was refluxed for 1 hour, whilethe resulted water together with about 12 ml of toluene were distilledoff outside the reaction system. After the remaining solvent in themixture was removed by a rotary evaporator under vacuo, 4.49 g (22 mmol) of 2,2-dimethyl-6-phenyl-4H-1,3-dioxin-4-one, 4.65 g (40 m mol) ofN,N,N',N'-tetramethylethylenediamine and 20 ml of xylene were added tothe residue. While further refluxing gently for 1.5 hours, the resultedacetone was removed to outside the reaction system. The mixture wascooled to precipitate the crystals. The crystals were filtered and driedto afford 2.63 g of the title compound (yield: 77.5%).

EXAMPLE 5 N-(2-Ethylphenyl)-2,5,6-trimethyl-4-oxo-4H-pyran-3-carboxamide(Compound No. 5)

A mixture of 2.21 g (10.8 m mol) of N-(2-ethylphenyl)-3-oxo-butanamide,0.96 g (16.0 m mol) of N,N-dimethylhydrazine and 30 ml of toluene wasstirred for 8 hours at 60° C. and further heated to a more elevatedtemperature to distill off the unreacted N,N-dimethylhydrazine and theresulted water together with 12 ml of toluene. The solvent was removedunder vacuo by a rotary evaporator. To the residue were added 2.10 g(14.5 m mol) of 2-methyl-3-oxo-ethylbutyrate, 10 g of molecular sieve 5Aand 30 ml of xylene. After refluxing for 8 hours, 10 g of molecularsieve 5A was further added and refluxed for 7 hours. The reactionmixture was filtered and concentrated to about 10 ml and cooled to roomtemperature. The precipitated crystals were filtered and dried to afford1.89 g of the title compound (yield: 62%).

EXAMPLES 6-139

Compound Nos. 6-139 were obtained by the method as described in thecolumn "Method", and Physico-chemical data on Compounds Nos. 1-139 areshown in Tables 1 and 2.

                                      TABLE 1                                     __________________________________________________________________________    Comp.                                      Melting                                                                             Molecular                    No. R.sub.1   R.sub.2                                                                              R.sub.3                                                                           R.sub.4                                                                            R.sub.5                                                                           R.sub.6                                                                           Method                                                                             point(°C.)                                                                   formula                      __________________________________________________________________________    1   ethyl     H      H   H    H   methyl                                                                            A    154.5-156                                                                           C.sub.15 H.sub.15                                                             NO.sub.3                     2   propyl    "      "   "    "   "   C    133-134                                                                             C.sub.16 H.sub.17                                                             NO.sub.3                     3   "         2-C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                 "    CH.sub.3                                                                          "   C    59.5-61                                                                             C.sub.21 H.sub.27                                                             NO.sub.3                     4   methyl    4-Cl   H   "    H   phenyl                                                                            D    220-224                                                                             C.sub.19 H.sub.14                                                             ClNO.sub.3                   5   "         2-C.sub.2 H.sub.5                                                                    "   "    CH.sub.3                                                                          methyl                                                                            E    179-182                                                                             C.sub.17 H.sub.19                                                             NO.sub.3                     6   butyl     H      "   "    H   "   C    99.5-101                                                                            C.sub.17 H.sub.19                                                             NO.sub.3                     7   isobutyl  "      "   "    "   "   "    116-117                                                                             C.sub.17 H.sub.19                                                             NO.sub.3                     8   pentyl    "      "   "    "   "   "    93.5-94.5                                                                           C.sub.18 H.sub.21                                                             NO.sub.3                     9   heptyl    "      "   "    "   "   "    77-79 C.sub.20 H.sub.25                                                             NO.sub.3                     10  phenyl    "      "   "    "   "   "    222-226                                                                             C.sub.19 H.sub.15                                                             NO.sub.3                     11  3-methylphenyl                                                                          H      H   H    H   methyl                                                                            C    154.5-156.5                                                                         C.sub.20 H.sub.17                                                             NO.sub.3                     12  4-methylphenyl                                                                          "      "   "    "   "   "    211.5-215.0                                                                         C.sub.20 H.sub.17                                                             NO.sub.3                     13  3-chlorophenyl                                                                          "      "   "    "   "   "    180-181                                                                             C.sub.19 H.sub.14                                                             ClNO.sub.3                   14  4-chlorophenyl                                                                          "      "   "    "   "   "    192-192.5                                                                           C.sub.19 H.sub.14                                                             ClNO.sub.3                   15  3-bromophenyl                                                                           "      "   "    "   "   "    175-176                                                                             C.sub.19 H.sub.14                                                             BrNO.sub.3                   16  3-trifluoro-                                                                            "      "   "    "   "   "    165-166.5                                                                           C.sub.20 H.sub.14                                                             F.sub.3 NO.sub.3                 methylphenyl                                                              17  phenylmethyl                                                                            "      "   "    "   "   "    137-139                                                                             C.sub.20 H.sub.17                                                             NO.sub.3                     18  3-pyridyl "      "   "    "   "   "    155-157                                                                             C.sub.18 H.sub.14                                                             N.sub.2 O.sub.3              19  trifluoromethyl                                                                         "      "   "    "   "   "    163-165                                                                             C.sub.14 H.sub.10                                                             F.sub.3 NO.sub.3             20  propyl    "      2-CH.sub.3                                                                        "    "   "   "    118.5-120.5                                                                         C.sub.17 H.sub.19                                                             NO.sub.3                     21  phenyl    2-CH.sub.3                                                                           H   H    H   methyl                                                                            C    135-136                                                                             C.sub.20 H.sub.17                                                             NO.sub.3                     22  "         2-Cl   "   "    "   "   "    168-170                                                                             C.sub.19 H.sub.14                                                             ClNO.sub.3                   23  propyl    2-CH.sub.3                                                                           3-CH.sub.3                                                                        "    "   "   "    133-135                                                                             C.sub.18 H.sub.21                                                             NO.sub.3                     24  butyl     "      "   "    "   "   "    82-84 C.sub.19 H.sub.23                                                             NO.sub.3                     25  pentyl    "      "   "    "   "   "    78-81 C.sub.20 H.sub.25                                                             NO.sub.3                     26  phenyl    "      "   "    "   "   "    164-166                                                                             C.sub.21 H.sub.19                                                             NO.sub.3                     27  "         "      6-CH.sub.3                                                                        "    "   "   "    201.5-202.5                                                                         C.sub.21 H.sub.19                                                             NO.sub.3                     28  propyl    2-C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                 "    "   "   "    63-69.5                                                                             C.sub.20 H.sub.25                                                             NO.sub.3                     29  butyl     "      "   "    "   "   "    oil   C.sub.21 H.sub.27                                                             NO.sub.3                     30  isobutyl  "      "   "    "   "   "    "     C.sub.21 H.sub.27                                                             NO.sub.3                     31  pentyl    2-C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                 H    H   methyl                                                                            C    oil   C.sub.22 H.sub.29                                                             NO.sub.3                     32  phenyl    "      "   "    "   "   "    186-189                                                                             C.sub.23 H.sub.23                                                             NO.sub.3                     33  propyl    "      "   4-Br "   "   "    76-77.5                                                                             C.sub.20 H.sub.24                                                             BrNO.sub.3                   34  methyl    H      H   H    CH.sub.3                                                                          "   E    190-191                                                                             C.sub.15 H.sub.15                                                             NO.sub.3                     35  3-chlorophenyl                                                                          "      "   "    "   "   C    173.5-175                                                                           C.sub. 20 H.sub.16                                                            ClNO.sub.3                   36  methyl    2-CH.sub.3                                                                           3-CH.sub.3                                                                        "    "   "   E    205.0-207.0                                                                         C.sub.17 H.sub.19                                                             NO.sub.3                     37  butyl     "      "   "    "   "   C    98-99.5                                                                             C.sub.20 H.sub.25                                                             NO.sub.3                     38  methyl    2-CH.sub.3                                                                           3-Cl                                                                              "    "   "   E    170-171                                                                             C.sub.16 H.sub.16                                                             ClNO.sub.3                   39  "         2-Cl   6-CH.sub.3                                                                        "    "   "   "    154-157                                                                             C.sub.16 H.sub.16                                                             ClNO.sub.3                   40  4-methylphenyl                                                                          2-C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                 "    H   "   C    181-183.5                                                                           C.sub.24 H.sub.25                                                             NO.sub.3                     41  methyl    2-C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                 H    CH.sub.3                                                                          methyl                                                                            E    74-75 C.sub.19 H.sub.23                                                             NO.sub.3                     42  ethyl     "      "   "    "   "   C    oil   C.sub.20 H.sub.25                                                             NO.sub.3                     43  butyl     "      "   "    "   "   "    "     C.sub.22 H.sub.29                                                             NO.sub.3                     44  pentyl    "      "   "    "   "   "    "     C.sub.23 H.sub.31                                                             NO.sub.3                     45  nonyl     "      "   "    "   "   E    "     C.sub.27 H.sub.39                                                             NO.sub.3                     46  phenylmethyl                                                                            "      "   "    "   "   "    "     C.sub.25 H.sub.27                                                             NO.sub.3                     47  phenyl    "      "   "    "   "   C    196.5-198                                                                           C.sub.24 H.sub.25                                                             NO.sub.3                     48  methyl    "      "   "    C.sub.2 H.sub.5                                                                   "   E    65-68 C.sub.20 H.sub.25                                                             NO.sub.3                     49  "         "      "   "    ph- "   "    95-96 C.sub.25 H.sub.27                                                             NO.sub.3                                                   CH.sub.2                                        50  "         "      "   "    (CH.sub.2).sub.4                                                                      "    115-117                                                                             C.sub.21 H.sub.25                                                             NO.sub.3                     51  propyl    2-C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                 4-Br CH.sub.3                                                                          methyl                                                                            C    70-71.5                                                                             C.sub.21 H.sub.26                                                             BrNO.sub.3                   52  methyl    H      H   H    H   tri-                                                                              E    174-175                                                                             C.sub.14 H.sub.10                                                             F.sub.3 NO.sub. 3                                              fluoro-                                                                       methyl                                      53  "         "      "   "    "   ethyl                                                                             "    137.5-138                                                                           C.sub.15 H.sub.15                                                             NO.sub.3                     54  "         "      "   "    "   pro-                                                                              "    133-134                                                                             C.sub.16 H.sub.17                                                             NO.sub.3                                                       pyl                                         55  "         "      "   "    "   phenyl                                                                            "    165-167                                                                             C.sub.19 H.sub.15                                                             NO.sub.3                     56  ethyl     "      "   "    "   ethyl                                                                             "    114.5-116                                                                           C.sub.16 H.sub.17                                                             NO.sub.3                     57  propyl    "      "   "    "   pro-                                                                              "    103.5-105                                                                           C.sub.18 H.sub.21                                                             NO.sub.3                                                       pyl                                         58  "         2-CH.sub.3                                                                           "   "    "   "   "    oil   C.sub.19 H.sub.23                                                             NO.sub.3                     59  methyl    2-C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                 "    "   ethyl                                                                             "    "     C.sub.19 H.sub.23                                                             NO.sub.3                     60  "         "      "   "    "   pro-                                                                              "    93-94 C.sub.20 H.sub.25                                                             NO.sub.3                                                       pyl                                         61  methyl    2-C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                 H    H   butyl                                                                             E    84-85 C.sub.21 H.sub.27                                                             NO.sub.3                     62  "         "      "   "    "   tri-                                                                              "    140-141                                                                             C.sub.18 H.sub.18                                                             F.sub.3 NO.sub.3                                               fluoro-                                                                       methyl                                      63  "         "      "   "    "   phenyl                                                                            "    114-118                                                                             C.sub.23 H.sub.23                                                             NO.sub.3                     64  ethyl     "      "   "    "   ethyl                                                                             "    oil   C.sub.20 H.sub.25                                                             NO.sub.3                     65  propyl    "      "   "    "   "   "    "     C.sub.21 H.sub.27                                                             NO.sub.3                     66  "         "      "   "    C.sub.2 H.sub.5                                                                   methyl                                                                            C    "     C.sub.22 H.sub.29                                                             NO.sub.3                     67  "         "      "   "    H   phenyl                                                                            E    105-108                                                                             C.sub.25 H.sub.27                                                             NO.sub.3                     68                                                                                 ##STR10##                                                                              H      H   H    "   methyl                                                                            C    220.5-221                                                                           C.sub.18 H.sub.14                                                             N.sub.2 O.sub.4              69  CH.sub.3  2-C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                 4-Br CH.sub.3                                                                          CH.sub.3                                                                          "    137-139.5                                                                           C.sub.19 H.sub.22                                                             BrNO.sub.3                   70  nC.sub.4 H.sub.9                                                                        "      "   "    H   "   "    69-72.5                                                                             C.sub.21 H.sub.26                                                             BrNO.sub.3                   71  1-bromobutyl                                                                            2-C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                 H    H   CH.sub.3                                                                          C          C.sub.21 H.sub.26                                                             BrNO.sub.3                   72  "         "      "   4-Br "   "   "          C.sub.21 H.sub.25                                                             Br.sub.2 NO.sub.3            73  nC.sub.3 H.sub.7                                                                        2-CHBrCH.sub.3                                                                       "   H    CH.sub.3                                                                          "   "          C.sub.21 H.sub.26                                                             BrNO.sub.3                   74  nC.sub.4 H.sub.9                                                                        "      "   "    "   "   "          C.sub.22 H.sub.28                                                             BrNO.sub.3                   75  "         2-C.sub.2 H.sub.5                                                                    "   4-Br "   "   "    82.5-84                                                                             C.sub.22 H.sub.28                                                             BrNO.sub.3                   76  3-nitrophenyl                                                                           H      H   H    H   "   "    181.5-183                                                                           C.sub.19 H.sub.14                                                             N.sub.2 O.sub.5              77  3-chlorophenyl                                                                          2-CH.sub.3                                                                           "   "    "   "   "    145-145.5                                                                           C.sub.20 H.sub.16                                                             ClNO.sub.3                   78  "         2-Cl   "   "    "   "   "    176-177                                                                             C.sub.19 H.sub.13                                                             Cl.sub.2 NO.sub.3            79  3-chlorophenyl                                                                          3-Cl   "   "    "   "   "    123.5-125                                                                           C.sub.19 H.sub.13                                                             Cl.sub.2 NO.sub.3            80  "         3-CF.sub.3                                                                           "   "    "   "   "          C.sub.20 H.sub.13                                                             ClF.sub.3 NO.sub.3           81  3-chlorophenyl                                                                          3-Br   H   H    H   CH.sub.3                                                                          C    140-141                                                                             C.sub.19 H.sub.13                                                             BrClNO.sub.3                 82  "         4-CH.sub.3                                                                           "   "    "   "   "    183.5-184                                                                           C.sub.20 H.sub.16                                                             ClNO.sub.3                   83  "         4-Cl   "   "    "   "   "    177-178                                                                             C.sub.19 H.sub.13                                                             Cl.sub.2 NO.sub.3            84  "         4-CF.sub.3                                                                           "   "    "   "   "    179-181                                                                             C.sub.20 H.sub.13                                                             ClF.sub.3 NO.sub.3           85  "         2-CH.sub.3                                                                           3-CH.sub.3                                                                        "    "   "   "    151.5-153                                                                           C.sub.21 H.sub.18                                                             ClNO.sub.3                   86  "         2-C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                 "    "   "   "    179.5-181.5                                                                         C.sub.23 H.sub.22                                                             ClNO.sub.3                   87  3-trifluoro-                                                                            4-F    H   "    "   "   "    191-197                                                                             C.sub.20 H.sub.13                                                             F.sub.4 NO.sub.3                 methylphenyl                                                              88  3-chlorophenyl                                                                          H      "   "    "   C.sub.2 H.sub.5                                                                   "    120-121                                                                             C.sub.20 H.sub.16                                                             ClNO.sub.3                   89  2-methoxymethyl                                                                         2-C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                 4-Br "   methyl                                                                            D    97-98.5                                                                             C.sub.19 H.sub.22                                                             NO.sub.4                     90  4-fluorophenyl                                                                          H      H   H    "   "   "    202.5-206.5                                                                         C.sub.19 H.sub.14                                                             FNO.sub.3                    91  4-fluorophenyl                                                                          3-CF.sub.3                                                                           H   H    H   methyl                                                                            D    178-179.5                                                                           C.sub.20 H.sub.13                                                             F.sub.4 NO.sub.3             92  butyl     2-C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                 4-Br CH.sub.3                                                                          ethyl                                                                             "          C.sub.23 H.sub.30                                                             BrNO.sub.3                   93  "         "      "   "    C.sub.2 H.sub.5                                                                   methyl                                                                            "          C.sub.23 H.sub.30                                                             BrNO.sub.3                   94  3-chlorophenyl                                                                          2-F    4-F H    H   "   D    72.5-73.0                                                                           C.sub.19 H.sub.12                                                             ClF.sub.2 NO.sub.3           95  2-methoxymethyl                                                                         2-C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                 4-Br CH.sub.3                                                                          methyl                                                                            D    97-100                                                                              C.sub.20 H.sub.24                                                             BrNO.sub.4                   96  "         "      "   H    "   "   "          C.sub.20 H.sub.25                                                             NO.sub.4                     97  "         "      "   "    H   "   "          C.sub.19 H.sub.23                                                             NO.sub.4                     98  propyl    2-C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                 4-C.sub.2 H.sub.5                                                                  "   "   "          C.sub.22 H.sub.29                                                             NO.sub.3                     99  "         "      "   "    CH.sub.3                                                                          "   "          C.sub.23 H.sub.31                                                             NO.sub.3                     100 "         "      "   4-Br "   ethyl                                                                             "          C.sub.22 H.sub.28                                                             BrNO.sub.3                   101 propyl    2-C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                 4-I  H   methyl                                                                            D    76-76.5                                                                             C.sub.20 H.sub.24                                                             INO.sub.3                    102 "         "      "   4-Br C.sub.2 H.sub.5                                                                   "   "          C.sub.22 H.sub.28                                                             BrNO.sub.3                   103 "         "      "   4-I  CH.sub.3                                                                          "   "    95.5-99                                                                             C.sub.21 H.sub.26                                                             INO.sub.3                    104 trifluoromethyl                                                                         "      "   H    H   "   "    182-183                                                                             C.sub.18 H.sub.18                                                             F.sub.3 NO.sub.3             105 propyl    "      "   4-OCH.sub.3                                                                        "   "   "          C.sub.21 H.sub.27                                                             NO.sub.4                     106 "         "      "   H    (CH.sub.2).sub.4                                                                      "                                       107 "         "      "   4-OCH.sub.3                                                                        CH.sub.3                                                                          methyl                                                                            "          C.sub.22 H.sub.29                                                             NO.sub.4                     108 "         "      "   4-NO.sub.2                                                                         H   "   "          C.sub.20 H.sub.24                                                             N.sub.2 O.sub.5              109 propyl    "      "   "    CH.sub.3                                                                          "   "          C.sub.22 H.sub.26                                                             N.sub.2 O.sub.5              110 methyl    "      "   H    nC.sub.3 H.sub.7                                                                  "   "          C.sub.21 H.sub.27                                                             NO.sub.3                     111 propyl    2-C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                 4-oph                                                                              H   methyl                                                                            D          C.sub.26 H.sub.29                                                             NO.sub.4                     112 "         "      "   "    CH.sub.3                                                                          "   "          C.sub.27 H.sub.31                                                             NO.sub.4                     113 methyl    "      "   4-Br nC.sub.3 H.sub.7                                                                  "   "    129.5-131.5                                                                         C.sub.21 H.sub.26                                                             BrNO.sub.3                   114 "         "      "   H    nC.sub.4 H.sub.9                                                                  "   "          C.sub.22 H.sub.29                                                             NO.sub.3                     115 "         2-CH.sub.3                                                                           3-CH.sub.3                                                                        "    C.sub.2 H.sub.5                                                                   "   "    193.5-196.0                                                                         C.sub.18 H.sub.21                                                             NO.sub.3                     118 "         "      "   4-Br nC.sub.3 H.sub.7                                                                  "   "    80.5-82.5                                                                           C.sub.23 H.sub.30                                                             BrNO.sub.3                   119 methyl    "      "   H    iso-                                                                              "   "          C.sub.22 H.sub.29                                                             NO.sub.3                                                   C.sub.4 H.sub.9                                 120 propyl    "      "   4-Br nC.sub.4 H.sub.9                                                                  "   "          C.sub.24 H.sub.32                                                             BrNO.sub.3                   121 propyl    2-C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                 4-Br iso-                                                                              methyl                                                                            D    72-76 C.sub.24 H.sub.32                                                             BrNO.sub.3                                                 C.sub.4 H.sub.9                                 122 "         "      "   4-NH.sub.2                                                                         CH.sub.3                                                                          "   "          C.sub.21 H.sub.28                                                             N.sub.2 O.sub.3              123 "         "      "   4-OC.sub.2 H.sub.5                                                                 H   "   "          C.sub.22 H.sub.29                                                             NO.sub.4                     124 "         "      "   "    CH.sub.3                                                                          "   "    82-84 C.sub.23 H.sub.31                                                             NO.sub.4                     125 "         "      "   4-nC.sub.3 H.sub.7                                                                 "   "   "          C.sub.24 H.sub.33                                                             NO.sub.3                     126 methyl    "      "   H    iso-                                                                              "   "          C.sub.23 H.sub.31                                                             NO.sub.3                                                   C.sub.5 H.sub.11                                127 propyl    "      "   4-Cl CH.sub.3                                                                          "   "    54.5-57.0                                                                           C.sub.21 H.sub.26                                                             ClNO.sub.3                   128 "         "      "   "    H   "   "          C.sub.20 H.sub.24                                                             ClNO.sub.3                   129 "         "      "   4-CH.sub.3                                                                         CH.sub.3                                                                          "   "    96-98 C.sub.22 H.sub.29                                                             NO.sub.3                     130 "         "      "   "    H   "   "          C.sub.21 H.sub.27                                                             NO.sub.3                     131 propyl    2-C.sub.2 H.sub.5                                                                    6-C.sub.2 H.sub.5                                                                 4-COOH                                                                             CH.sub.3                                                                          methyl                                                                            D          C.sub.22 H.sub.27                                                             NO.sub.5                     132 "         "      "   "    H   "   "          C.sub.21 H.sub.25                                                             NO.sub.5                     133 "         "      "   4-CN CH.sub.3                                                                          "   "          C.sub.22 H.sub.26                                                             N.sub.2 O.sub.3              134 "         "      "   "    H   "   "    67-69 C.sub.21 H.sub.24                                                             N.sub.2 O.sub.3              135 ethyl     "      "   4-Br CH.sub.3                                                                          "   "    109-112                                                                             C.sub.20 H.sub.24                                                             BrNO.sub.3                   136 propyl    "      "   "    (CH.sub.2).sub.4                                                                      E    101-102                                                                             C.sub.23 H.sub.28                                                             BrNO.sub.3                   137 "         "      "   "    (CH.sub.2).sub.3                                                                      "    90-92 C.sub.22 H.sub.26                                                             BrNO.sub.3                   138 "         "      "   4-COOEt                                                                            H   methyl                                                                            D           C.sub.23 H.sub.29                                                            NO.sub.5                     139 "         "      "   "    CH.sub.3                                                                          "   "          C.sub.24 H.sub.31                                                             NO.sub.5                     __________________________________________________________________________

                                      TABLE 2                                     __________________________________________________________________________    Compound                                                                            IR           NMR                                                        No.   ν value (cm.sup.-1)                                                                Method                                                                             Chemical shift δ value                                                                         Solvent                             __________________________________________________________________________                       1.31(t,3H), 2.27(s,3H),                                                       3.28(q,2H), 6.18(s,1H),                                    1     1650, 1700                                                                            KBr  6.90-7.70(m,5H), and   CDCl.sub.3                                             11.90(br,1H)                                                                  1.02(t,3H), 1.75(six,2H),                                                     2.38(s,3H), 3.23(t,2H),                                    2     1657, 1697                                                                            "    6.18(s,1H), 6.90-7.70(m,5H),                                                                         "                                                      and 11.92(br,1H)                                                              0.98(t,3H), 1.16(t,6H),                                                       1.75(six,2H), 2.00(s,3H),                                  3     1650, 1680                                                                            "    2.32(s,3H), 2.62(q,4H),                                                                              "                                                      3.20(t,2H), 7.04(s,3H),                                                       and 11.10(br,1H)                                                              2.97(s,3H), 6.38(s,1H),                                                       7.10-7.83(m,9H), and                                       4     1638, 1685                                                                            "    12.10(br,1H)           "                                                      1.26(t,3H), 1.95(s,3H),                                                       2.26(s,3H), 2.75(q,2H),                                    5     1650, 1692                                                                            "    2.79(s,3H), 6.70-8.20(m,4H),                                                                         "                                                      and 12.20(br,1H)                                                              0.70-2.00(m,7H), 2.28(s,3H),                                                  3.27(t,2H), 6.19(s,1H),                                    6     1657, 1707                                                                            KBr  6.90-7.70(m,5H), and   CDCl.sub.3                                             11.90(br,1H)                                                                  0,97(d,6H), 2.27(s,3H),                                                       2.30(m,1H), 3.18(d,2H),                                    7     1620, 1660,                                                                           "    6.20(s,1H), 6.95- 7.70(m,5H),                                                                        "                                         1690         and 11.87(br,1H)                                                              0.70-2.00(m,9H), 2.24(s,3H),                                                  3.27(t,2H), 6.16(s,1H),                                    8     1655, 1705                                                                            "    6.90-7.70(m,5H), and   "                                                      11.86(br,1H)                                                                  0.70-2.00(m,13H), 2.29(s,3H),                                                 3.30(t,2H), 6.23(s,1H),                                    9     1653, 1705                                                                            "    7.00-7.77(m,5H), and   "                                                      11.87(br,1H)                                                                  2.36(s,3H), 6.28(s,1H),                                                       6.80-7.80(m,10H),                                          10    1607, 1655,                                                                           "    and 10.23(br,1H)       DMSO--d.sup.6                             1675                                                                                       2.30(s,3H), 2.36(s,3H),                                                       6.25(s,1H), 6.90-7.60(m,9H),                               11    1603, 1650,                                                                           KBr  and 10.95(br,1H)       CDCl.sub.3                                1673                                                                                       2.30(s,3H), 2.34(s,3H),                                                       6.24(s,1H), 6.90-7.60(m,9H),                               12    1657, 1680                                                                            "    and 10.92(br,1H)       "                                                      2.34(s,3H), 6.33(s,1H),                                                       7.00-7.67(m,9H),                                           13    1627, 1673                                                                            "    and 11.14(br,1H)       "                                                      2.30(s,3H), 6.26(s,1H),                                                       6.90-7.60(m,9H),                                           14    1655, 1680                                                                            "    and 11.12(br,1H)       "                                                      2.35(s,3H), 6.32(s,1H),                                                       6.95-7.67(m,9H),                                           15    1605, 1625,                                                                           "    and 11.19(br,1H)       "                                         1670                                                                                       2.33(s,3H), 6.33(s,1H),                                                       6.90-7.80(m,9H),                                           16    1650, 1675                                                                            KBr  and 11.23(br,1H)       CDCl.sub.3                                1695                                                                                       2.20(s,3H), 4.66(s,2H),                                                       6.13(s,1H), 6.95-7.70(m,10H),                              17    1653, 1703                                                                            "    and 11.92(br,1H)       "                                                      2.33(s,3H), 6.31(s,1H),                                                       6.90-8.70(m,9H),                                           18    1617, 1650,                                                                           "    and 11.36(br,1H)       "                                         1690                                                                                       2.33(s,3H), 6.27(s,1H),                                                       6.85-7.65(m,5H),                                           19    1600, 1655,                                                                           "    and 9.42(br,1H)        "                                         1705                                                                                       1.00(t,3H), 1.75(six,2H),                                                     2.28(s,3H), 2.36(s,3H),                                    20    1620, 1657,                                                                           "    3.23(t,2H), 6.16(s,1H),                                                                              "                                         1697         6.80-8.10(m,4H), and                                                          11.76(br,1H)                                                                  2.32(s,3H), 2.36(s,3H),                                                       6.32(s,1H), 6.85-8.10(m,9H),                               21    1620, 1660,                                                                           KBr  and 10.90(br,1H)       CDCl.sub.3                                1707                                                                                       2.34(s,3H), 6.31(s,1H),                                                       6.80-8.32(m,9H),                                           22    1655, 1700                                                                            "    and 10.23(br,1H)       "                                                      1.02(t,3H), 1.68(six,2H),                                                     2.25(s,3H), 2.29(s,6H),                                    23    1620, 1660,                                                                           "    3.26(t,2H), 6.21(s,1H),                                                                              "                                         1695         6.85-7.80(m,3H),                                                              and 11.60(br,1H)                                                              0.75-2.00(m,7H), 2.23(s,3H),                                                  2.27(s,6H), 3.27(t,3H),                                    24    1620, 1660,                                                                           "    6.19(s,1H), 6.80-7.83(m,3H),                                                                         "                                         1700         and 11.60(br,1H)                                                              0.70-2.00(m,9H), 2.26(s,3H),                                                  2.30(s,6H), 3.32(t,2H),                                    25    1620, 1660,                                                                           "    6.23(s,1H), 6.85-7.83(m,3H),                                                                         "                                         1697         and 11.64(br,1H)                                                              2.24(s,6H), 2.31(s,3H),                                                       6.23(s,1H), 6.70-7.65(m,8H),                               26    1657, 1697                                                                            KBr  and 10.47(br,1H)       CDCl.sub.3                                             2.24(s,6H), 2.36(s,3H),                                                       6.34(s,1H), 7.00-7.67(m,8H),                               27    1603, 1623,                                                                           "    and 9.98(br,1H)        "                                         1667                                                                                       0.98(t,3H), 1.17(t,6H),                                                       1.75(six,2H), 2.28(s,3H),                                  28    1627, 1640,                                                                           "    2.63(q,4H), 3.24(t,2H),                                                                              "                                         1670         6.24(s,1H), 7.06(s,3H),                                                       and 10.98(br,1H)                                                              0.60-2.00(m,7H), 1.17(t,6H),                                                  2.28(s,3H), 2.60(q,4H),                                    29    1660, 1687                                                                            neat 3.23(t,2H), 6.20(s,1H),                                                                              "                                                      7.05(s,3H), and                                                               10.80(br,1H)                                                                  0.97(d,6H), 1.19(t,6H),                                                       2.30(m,1H), 2.32(s,3H),                                    30    1600, 1657,                                                                           "    2.64(q,4H), 3.22(d,2H),                                                                              "                                         1685         6.29(s,1H), 7.12(s,3H),                                                       and 11.00(br,1H)                                                              0.60-2.00(m,9H), 1.20(t,6H),                                                  2.32(s,3H), 2.63(q,4H),                                    31    1610, 1660,                                                                           neat 3.28(t,2H), 6.27(s,1H),                                                                              CDCl.sub.3                                1687         7.12(s,3H), and                                                               11.00(br,1H)                                                                  1.16(t,6H), 2.32(s,3H),                                                       2.58(q,4H), 6.27(s,1H),                                    32    1603, 1623,                                                                           KBr  7.00-7.50(m,8H),       "                                         1647, 1663   and 9.87(br,1H)                                                               0.98(t,3H), 1.16(t,6H),                                                       1.75(six,2H), 2.30(s,3H),                                  33    1640, 1683                                                                            "    2.67(q,4H), 3.20(t,2H),                                                                              "                                                      6.23(s,1H), 7.18(s,2H),                                                       and 11.03(br,1H)                                                              1.96(s,3H), 2.32(s,3H),                                                                              CDCl.sub.3 +                                           2.80(s,3H), 6.90-7.70(m,5H),                               34    1647, 1683                                                                            "    and 12.17(br,1H)       DMSO--d.sup.6                                          2.06(s,3H), 2.39(s,3H),                                                       7.00-7.10(m,9H),                                           35    1620, 1645,                                                                           "    and 11.40(br,1H)       CDCl.sub.3                                1695                                                                                       1.96(s,3H), 2.26(s,9H),                                                       2.78(s,3H), 6.80-7.80(m,3H),                               36    1610, 1653,                                                                           KBr  and 11.96(br,1H)       CDCl.sub.3                                1690                                                                                       0.65-2.00(m,7H), 1.98(s,3H),                                                  2.26(s,9H), 3.27(t,2H),                                    37    1615, 1645,                                                                           "    6.70-7.80(m,3H),       "                                         1693         and 11.80(br,1H)                                                              1.94(s,3H), 2.28(s,3H),                                                       2.41(s,3H), 2.78(s,3H),                                    38    1660, 1700                                                                            "    7.90-8.00(m,3H),       "                                                      and 12.15(br,1H)                                                              1.98(s,3H), 2.27(s,3H),                                                       2.30(s,3H), 2.76(s,3H),                                    39    1653, 1677                                                                            "    6.90-7.30(m,3H),       "                                                      and 11.60(br,1H)                                                              1.16(t,6H), 2.30(s,3H),                                          1610, 1625,  2.33(s,3H), 2.59(q,4H),                                    40    1647, 1660,                                                                           "    6.25(s,1H), 6.90-7.50(m,7H),                                                                         "                                         1680         and 9.90(br,1H)                                                               1.20(t,6H), 2.00(s,3H),                                                       2.32(s,3H), 2.62(q,4H),                                    41    1653, 1680                                                                            KBr  2.80(s,3H), 7.10(s,3H),                                                                              CDCl.sub.3                                             and 11.33(br,1H)                                                              1.14(t,6H), 1.28(t,3H),                                                       1.98(s,3H), 2.31(s,3H),                                    42    1613, 1652,                                                                           neat 2.60(q,4H), 3.12(q,2H),                                                                              "                                         1680         7.03(s,3H), and                                                               11.18(br,1H)                                                                  0.80-2.00(m,7H), 1.17(t,6H),                                                  2.00(s,3H), 2.32(s,3H),                                    43    1655, 1680                                                                            "    2.61(q,4H), 3.20(t,2H),                                                                              "                                                      7.04(s,3H), and                                                               11.13(br,1H)                                                                  0.80-2.00(m,9H), 1.16(t,6H),                                                  2.00(s,3H), 2.32(s,3H),                                    44    1657, 1680                                                                            "    2.62(q,4H), 3.20(t,2H),                                                                              "                                                      7.03(s,3H), and                                                               11.12(br,1H)                                               45    1655, 1683                                                                            "    --                                                         46    1657, 1683                                                                            neat --                                                                            1.14(t,6H), 2.05(s,3H),                                                       2.36(s,3H), 2.58(q,4H),                                    47    1620, 1660                                                                            KBr  7.00-7.60(m,8H),       CDCl.sub.3                                             and 10.10(br,1H)                                                              1.04(t,3H), 1.16(t,6H),                                                       2.32(s,3H), 2.47(q,2H),                                    48    1643, 1673                                                                            "    2.63(q,4H), 2.76(s,3H),                                                                              "                                                      7.03(s,3H), and                                                               11.37(br,1H)                                                                  1.13(t,6H), 2.25(s,3H),                                                       2.60(q,4H), 2.73(s,3H),                                    49    1640, 1717                                                                            "    3.81(s,2H), 7.05(s,3H),                                                                              "                                                      7.15(s,5H), and                                                               11.25(br,1H)                                                                  1.16(t,6H), 1.40-2.85(m,8H),                                                  2.59(q,4H), 2.76(s,3H),                                    50    1655, 1677                                                                            "    7.01(s,3H), and        "                                                      11.23(br,1H)                                                                  0.98(t,3H), 1.19(t,6H),                                                       1.75(six,2H), 2.00(s,3H),                                  51    1637, 1667                                                                            KBr  2.33(s,3H), 2.60(q,4H),                                                                              CDCl.sub.3                                             3.20(t,2H), 7.20(s,2H),                                                       and 11.30(br,1H)                                                              2.86(s,3H), 6.73(s,1H),                                                       6.90-7.70(m,5H),                                           52    1695    "    and 11.43(br,1H)       "                                                      1.23(t,3H), 2.57(q,2H),                                                       2.82(s,3H), 6.20(s,1H),                                    53    1657, 1700                                                                            "    6.90-7.70(m,5H),       "                                                      and 11.95(br,1H)                                                              0.97(t,3H), 1.67(six,2H),                                                     2.47(t,2H), 2.80(s,3H),                                    54    1643, 1687                                                                            "    6.18(s,1H), 6.90-7.70(m,5H),                                                                         "                                                      and 12.07(br,1H)                                                              2.94(s,3H), 6.80(s,1H),                                                       6.90-7.70(m,10H), and                                      55    1600, 1620,                                                                           "    11.95(br,1H)           "                                         1640, 1690                                                                                 1.21(t,3H), 1.30(t,3H),                                                       2.54(q,2H), 3.27(q,2H),                                    56    1652, 1698                                                                            KBr  6.17(s,1H), 6.70-7.90(m,5H),                                                                         CDCl.sub.3                                             12.02(br,1H)                                                                  0.96(t,3H), 1.01(t,3H),                                                       1.67(six,2H), 1.80(six,2H),                                57    1620, 1647,                                                                           "    2.48(t,2H), 3.26(t,2H),                                                                              "                                         1690         6.18(s,1H), 6.90-7.75(m,5H),                                                  and 12.02(br,1H)                                           58    1655, 1690                                                                            neat --                                                                            1.13(t,6H), 1.23(t,3H),                                                       2.57(q,2H), 2.61(q,4H),                                    59    1652, 1685                                                                            "    2.75(s,3H), 6.23(s,1H),                                                                              CDCl.sub.3                                             7.03(s,3H), and                                                               11.03(br,1H)                                                                  0.96(t,3H), 1.20(t,6H),                                                       1.66(six,2H), 2.47(t,2H),                                  60    1650, 1675                                                                            KBr  2.63(q,4H), 2.80(s,3H),                                                                              "                                                      6.21(s,1H), 7.07(s,3H),                                                       and 11.16(br,1H)                                                              0.70-2.00(m,7H), 1.19(t,6H),                                                  2.50(t,2H), 2.63(q,4H),                                    61    1650, 1673                                                                            KBr  2.80(s,3H), 6.20(s,1H),                                                                              CDCl.sub.3                                             7.07(s,3H), and                                                               11.20(br,1H)                                                                  1.15(t,6H), 2.57(q,4H),                                                       2.84(s,3H), 6.77(s,1H),                                    62    1607, 1640,                                                                           "    7.04(s,3H), and        "                                         1650, 1675   10.25(br,1H)                                                                  1.19(t,6H), 2.63(q,4H),                                                       2.92(s,3H), 6.82(s,1H),                                    63    1610, 1640,                                                                           "    6.90-8.10(m,8H),       "                                         1673         and 11.12(br,1H)                                                              1.19(t,6H), 1.27(t,3H),                                                       1.30(t,3H), 2.45(q,2H),                                    64    1605, 1647,                                                                           neat 2.61(q,4H), 3.24(q,2H),                                                                              "                                         1680         6.20(s,1H), 7.04(s,3H),                                                       and 11.15(br,1H)                                                              0.97(t,3H), 1.18(t,6H),                                                       1.27(t,3H), 1.75(six,2H),                                  65    1653, 1685                                                                            "    2.60(q,2H), 2.62(q,4H),                                                                              "                                                      3.21(t,2H), 6.21(s,1H),                                                       7.05(s,3H), and 10.83(br,1H)                                                  0.96(t,3H), 1.09(t,3H),                                                       1.16(t,6H), 1.73(six,2H),                                  66    1650, 1680                                                                            neat 2.31(s,3H), 2.49(q,2H),                                                                              CDCl.sub.3                                             2.61(q,4H), 3.17(t,2H),                                                       7.04(s,3H), and 11.14(br,1H)                                                  1.07(t,3H), 1.20(t,6H),                                                       1.85(six,2H), 2.63(q,4H),                                  67    1615, 1643,                                                                           KBr  3.36(t,2H), 6.81(s,1H),                                                                              "                                         1680         7.05-7.85(m,8H), and                                                          11.23(br,1H)                                                                  2.40(s,3H), 6.36(s,1H),                                                                              CDCl.sub.3                                             6.95-8.40(m,9H),       +                                   68    1615, 1657,                                                                           "    and 10.90(br,1H)       DMSO-d.sup.6                              1707                                                                    __________________________________________________________________________    Compound                                                                            IR           NMR                                                        No.   ν value (cm.sup.-1)                                                                Method                                                                             Chemical shift ν value                                                                            Solvent                             __________________________________________________________________________                       1.16(t,6H), 1.99(s,3H), 2.33(s,3H),                        69    1657, 1680                                                                            KBr  2.57(q,4H), 2.78(s,3H), 7.18(s,2H), and                                                              CDCl.sub.3                                             11.25(br,1H)                                                                  0.60-2.00(m,7H), 1.17(t,6H), 2.31(s,3H),                   70    1637, 1685                                                                            "    2.58(q,4H), 3.22(t,2H), 6.24(s,1H),                                                                  "                                                      7.20(s,2H), and 11.00(br,1H)                                                  0.70-2.20(m,7H), 1.18(t,6H), 2.36(s,3H),                   71    1610, 1680                                                                            neat 2.60(q,4H), 6.26(s,1H), 6.69(t,1H),                                                                  "                                                      7.07(s,3H), and 10.83(br,1H)                               72    1610, 1657,                                                                           "    0.70-2.20(m,5H), 1.16(t,6H), 2.35(s,3H),                         1680         2.58(q,4H), 6.28(s,1H), 6.68(t,1H),                                                                  "                                                      7.20(s,2H), and 10.75(br,1H)                                                  0.70-2.20(m,7H), 1.17(t,3H), 1.62(d,3H),                   73    1620, 1660                                                                            "    1.92(s,3H), 2.25(s,3H), 2.50-3.10(m,4H),                                                             "                                                      5.47(q,1H), 6.90-7.30(m,3H), and 11.93(br,1H)                                 0.60-2.20(m,7H), 1.18(t,3H), 1.68(d,3H),                   74    1610, 1665                                                                            neat 1.93(s,3H), 2.28(s,3H), 2.50-3.10(m,4H),                                                             CDCl.sub.3                                             5.44(q,1H), 6.90-7.30(m,3H), and 12.00                                        (br,1H)                                                                       0.70-2.00(m,7H), 1.17(t,6H), 2.00(s,3H),                   75    1655, 1683                                                                            KBr  2.33(s,3H), 2.58(q,4H), 3.20(d,2H),                                                                  "                                                      7.18(s,2H), and 11.20(br,1H)                               76    1657, 1680,                                                                           "    2.34(s,3H), 6.38(s,1H), 6.90-7.45(m,9H),                                                             "                                         1695         and 11.38(br,1H)                                           77    1660, 1700                                                                            "    2.36(s,3H), 2.40(s,3H), 6.38(s,1H),                                                                  "                                                      6.90-8.05(m,8H), and 11.05(br,1H)                          78    1613, 1660,                                                                           "    2.31(s,3H), 6.28(s,1H), 6.70-8.23(m,8H),                                                             "                                         1700         and 11.60(br,1H)                                                              2.33(s,3H), 6.30(s,1H), 6.90-7.70(m,8H),                   79    1627, 1657,                                                                           KBr  and 11.37(br,1H)       CDCl.sub.3                                1670                                                                                       2.33(s,3H), 6.32(s,1H), 7.15-7.90(m,8H),                   80    1600, 1657,                                                                           neat and 11.50(br,1H)       "                                         1690                                                                                       2.33(s,3H), 6.30(s,1H), 7.00-7.80(m,8H),                                                             "                                   81    1660, 1695                                                                            KBr  and 11.37(br,1H)                                                              2.25(s,3H), 2.29(s,3H), 6.24(s,1H),                        82    1615, 1633,                                                                           "    6.85-7.50(m,8H), and 10.80(br,1H)                                                                    "                                         1673                                                                                       2.33(s,3H), 6.30(s,1H), 7.00-7.60(m,8H),                   83    1617, 1625,                                                                           "    and 11.30(br,1H)       "                                         1660, 1670                                                                                 2.36(s,3H), 6.33(s,1H), 7.20-7.80(m,8H),                   84    1615, 1657,                                                                           KBr  and 11.57(br,1H)       CDCl.sub.3                                1700                                                                                       2.28(s,6H), 2.33(s,3H), 6.30(s,1H),                        85    1623, 1660,                                                                           "    6.80-7.70(m,7H), and 10.70(br,1H)                                                                    "                                         1707                                                                                       1.16(t,6H), 2.31(s,3H), 2.59(q,4H),                        86    1645, 1663                                                                            "    6.30(s,1H), 6.90-7.50(m,7H), and                                                                     "                                                      10.05(br,1H)                                               87    1630, 1650,                                                                           "    2.36(s,3H), 6.35(s,1H), 6.70-7.80(m,8H),                                                             "                                         1665         and 11.34(br,1H)                                           88    1627, 1653,                                                                           "    1.25(t,3H), 2.61(q,2H), 6.29(s,1H),                                                                  "                                         1697         6.80-7.65(m,9H), and 10.97(br, 1H)                         __________________________________________________________________________    Compound                                                                            IR           NMR                                                        No.   ν value (cm.sup.-1)                                                                Method                                                                             Chemical shift δ value                                                                         Solvent                             __________________________________________________________________________                       1.17(t,6H), 2.40(s,3H),                                    89                 2.60(q,4H), 3.46(s,3H),                                                                              CDCl.sub.3                                             5.00(s,2H), 6.30(s,1H)                                                        7.23(s,2H), and 11.10(br,1H)                                                  2.36(s,3H), 6.26(s,1H),                                                                              CDCl.sub.3 +                        90    1610, 1620, 1663                                                                      KBr  6.80-7.80(m,9H) and                                                           10.47(br,1H)           DMSO--d.sup. 6                                         2.33(s,3H), 6.28(s,1H),                                    91    1610, 1620, 1663                                                                      "    6.87-7.80(m,8H) and    CDCl.sub.3                                             11.52(br,1H)                                                                  1.18(t,6H), 1.32(t,3H),                                    92    1653, 1683                                                                            neat 0.70-2.10(m,7H), 2.03(s,3H),                                                                         "                                                      2.62(q,4H), 2.73(q,2H),                                                       3.28(t,2H), 7.24(s,2H) and                                                    11.25(br,1H)                                                                  0.70-2.10(m,7H), 1.12(t,3H),                               93    1630, 1640, 1663                                                                      "    1.17(t,6H), 2.34(s,3H),                                                                              "                                                      2.50(q,2H), 2.62(q,4H),                                                       3.23(t,2H), 7.23(s,2H) and                                                    11.20(br,1H)                                               94    1613, 1660, 1697                                                                      KBr                                                                                1.17(t,6H), 2.03(s,3H),                                    95    1620, 1650, 1673                                                                      "    2.42(s,3H), 2.60(q,4H),                                                                              CDCl.sub.3                                             3.43(s,3H), 5.00(s,2H),                                                       7.23(s,2H) and 11.13(br,1H)                                                   1.17(t,6H), 2.02(s,3H),                                    96                 2.40(s,3H), 2.60(q,4H),                                                                              "                                                      3.43(s,3H), 4.98(s,2H),                                                       7.08(s,3H) and 11.14(br,1H)                                                   1.19(t,6H), 2.39(s,3H),                                    97                 2.61(q,4H), 3.47(s,3H),                                                                              "                                                      5.02(s,2H), 6.31(s,1H),                                                       7.11(s,3H) and 10.87(br,1H)                                                   1.00(t,3H), 1.17(t,6H),                                    98    1607, 1660, 1690                                                                      neat 1.22(t,3H), 1.75(six,2H),                                                                            "                                                      2.30(s,3H), 2.59(q,6H),                                                       3.21(t,2H), 6.21(s,1H),                                                       6.89(s,2H), and 10.73(br,1H)                                                  0.99(t,3H), 1.17(t,6H),                                                       1.23(t,3H), 1.77(six,2H),                                  99    1655, 1680                                                                            neat 2.02(s,3H), 2.34(s,3H),                                                                              CDCl.sub.3                                             2.60(q,6H), 3.20(t,2H),                                                       6.92(s,2H) and 11.03(br,1H)                                                   0.70-2.00(m,5H), 0.99(t,3H),                                                  1.17(t,6H), 2.02(s,3H),                                    100   1653, 1683                                                                            "    2.55(q,2H), 2.59(q,4H),                                                                              "                                                      3.20(t,2H), 7.21(s,2H),                                                       11.24(br,1H)                                                                  0.99(t,3H), 1.17(t,6H),                                                       1.75(six,2H), 2.31(s,3H)                                   101   1640, 1685                                                                            KBr  2.55 (q,4H), 3.20(t,2H),                                                                             "                                                      6.23(s,1H), 7.38(s,2H) and                                                    11.07(br,1H)                                                                  0.98(t,3H), 1.09(t,3H),                                                       1.15(t,6H), 1.74(six,2H),                                  102   1640, 1660, 1685                                                                      neat 2.32(s,3H), 2.45(q,2H),                                                                              "                                                      2.57(q,4H), 3.16(t,2H),                                                       7.17(s,2H) and 11.00(br,1H)                                                   0.96(t,3H), 1.14(t,6H),                                    103   1637, 1640, 1670                                                                      KBr  1.73(six,2H), 2.00(s,3H),                                                                            "                                                      2.33(s,3H), 2.55(q,4H),                                                       3.18(t,2H), 7.39(s,2H) and                                                    11.23(br,1H)                                                             CHCl.sub.3                                                                         1.18(t,6H), 2.40(s,3H),                                    104   1657    Soln.                                                                              2.64(q,4H), 6.32(s,1H),                                                                              CDCl.sub.3                                             7.08(m,3H) and 8.74(br,1H)                                                    0.98(t,3H), 1.26(t,6H),                                    105                1.75(six,2H), 2.30(s,3H),                                                                            "                                                      2.57(q,4H), 3.21(t,2H),                                                       3.76(s,3H), 6.23(s,1H),                                                       6.61(s,2H) and 10.75(br,1H)                                                   0.99(t,3H), 1.17(t,6H),                                                       1.40-2.00(m,6H), 2.35-2.55                                 106                (m,4H), 2.63(q,4H), 3.21(t,2H),                                                                      "                                                      7.10(t,3H) and 11.17(br,1H)                                                   0.98(t,3H), 1.17(t,6H),                                    107   1603, 1653, 1690                                                                      neat 1.73(six,2H), 2.00(s,3H),                                                                            "                                                      2.32(s,3H), 2.58(q,4H),                                                       3.20(t,2H), 3.76(s,3H),                                                       6.62(s,2H) and 10.98(br,1H)                                                   1.02(t,3H), 1.24(t,6H),                                                       1.78(six,2H), 2.36(s,3H),                                  108                2.73(q,4H), 3.26(t,2H),                                                                              "                                                      6.33(s,1H), 8.00(s,2H) and                                                    11.61(br,1H)                                                                  1.00(t,3H), 1.23(t,6H),                                                       1.76(six,2H), 2.02(s,3H),                                  109                2.37(s,3H), 2.73(q,4H),                                                                              CDCl.sub.3                                             3.23(t,2H), 7.97(s,2H) and                                                    11.78(br,1H)                                                                  0.98(t,3H), 1.19(t,6H),                                                       1.55(six,2H), 2.30(s,3H),                                  110   1655, 1687                                                                            neat 2.45(t,2H), 2.63(q,4H),                                                                              "                                                      2.76(s,3H), 7.09(s,3H) and                                                    11.30(br,1H)                                                                  1.01(t,3H), 1.14(t,6H),                                                       1.78(six,2H), 2.28(s,3H),                                  111                2.59(q,4H), 3.25(t,2H),                                                                              "                                                      6.26(s,1H), 6.85(s,2H), 6.80-                                                 7.50(m,5H) and 11.02(br,1H)                                                   0.98(t,3H), 1.14(t,6H),                                    112   1659, 1683                                                                            neat 1.75(six,2H), 2.00(s,3H),                                                                            "                                                      2.31(s,3H), 2.59(q,4H),                                                       3.21(t,2H), 6.85(s,2H), 6.80-                                                 7.50(m,5H) and 11.18(br,1H)                                                   0.98(t,3H), 1.19(t,6H),                                    113   1653, 1683                                                                            KBr  1.53(six,2H), 2.33(s,3H),                                                                            "                                                      2.47(t,2H), 2.60(q,4H),                                                       2.77(s,3H), 7.23(s,2H) and                                                    11.34(br,1H)                                                                  0.70-1.70(m,7H), 1.16(t,6H),                               114   1653, 1683                                                                            neat 2.30(s,3H), 2.45(t,2H),                                                                              CDCl.sub.3                                             2.63(q,4H), 2.75(s,3H),                                                       7.08(s,3H) and 11.27(br,1H)                                115   1655, 1695                                                                            KBr                                                                                0.98(t,6H), 1.16(t,6H),                                    118   1645, 1677                                                                            KBr  1.40-2.10(m,4H), 2.33(s,3H),                                                                         "                                                      2.47(t,2H), 2.60(q,4H),,                                                      3.20(t,2H), 7.20(s,2H) and                                                    11.21(br,1H)                                                                  0.95(d,6H), 1.18(t,6H),                                                       1.40-2.10(m,1H), 2.28(s,3H),                               119   1653, 1685                                                                            neat 2.50(d,2H), 2.63(q,4H),                                                                              CDCl.sub.3                                             2.75(s,3H), 7.08(s,3H,)                                                       and 11.30(br.1H)                                                              0.70-2.10(m,12H), 1.16(t,6H),                                                 2.32(s,3H), 2.40(t,2H),                                    120   1650, 1680                                                                            "    2.60(q,4H), 3.20(t,2H),                                                                              "                                                      7.20(s,2H), and                                                               11.31(br,1H)                                                                  0.94(d,6H), 0.98(t,3H),                                                       1.17(t,6H), 1.35-2.10(m,3H),                               121   1650, 1680                                                                            KBr  2.33(s,3H), 2.45(d,2H),                                                                              "                                                      2.58(q,4H), 3.20(t,2H),                                                       7.20(s,2H), and 11.30(br,1H)                                                  0.97(t,3H), 1.13(t,6H),                                                       1.75(six,2H), 1.99(s,3H),                                  122                2.32(s,3H), 2.52(q,4H),                                                                              "                                                      3.19(t,2H), 3.61(br,2H),                                                      6.42(s,2H), and 10.67(br,1H)                                                  0.98(t,3H), 1.16(t,6H),                                                       1.37(t,3H), 1.75(six,2H),                                  123   1603, 1660,                                                                           neat 2.28(s,3H), 2.55(q,4H),                                                                              "                                         1683         3.18(t,2H), 3.97(q,2H),                                                       6.18(s,1H), 6.58(s,2H),                                                       and 10.57(br,1H)                                                              0.98(t,3H), 1.18(t,6H),                                                       1.39(t,3H), 1.75(six,2H),                                  124   1650, 1680                                                                            KBr  2.00(s,3H), 2.58(q,4H),                                                                              CDCl.sub.3                                             3.18(t,2H), 3.98(q,2H),                                                       6.60(s,2H), 10.76(br,1H),                                                     and 2.33(s,3H)                                                                0.98(t,6H), 1.17(t,6H),                                                       1.40-2.10(m,4H), 2.00(s,3H),                               125                2.34(s,3H), 2.60(q,4H),                                                                              "                                                      3.20(t,2H), 6.88(s,2H),                                                       11.05(br,1H), and 2.53(t,2H)                                                  0.70-2.00(m,3H), 0.95(d,6H),                                                  1.17(t,6H), 2.30(s,3H),                                    126                2.41(t,2H), 2.60(q,4H),                                                                              "                                                      2.76(s,3H), 7.06(s,3H),                                                       and 11.27(br,1H)                                                              0.98(t,3H), 1.17(t,6H),                                                       1.75(six,2H), 2.00(s,3H),                                  127   1657, 1673                                                                            KBr  2.34(s,3H), 2.60(q,4H),                                                                              "                                                      3.21(t,2H), 7.07(s,2H), and                                                   11.23(br,1H),                                                                 0.98(t,3H), 1.17(t,6H),                                                       1.75(six,2H), 2.33(s,3H),                                  128   1657, 1683                                                                            neat 2.59(q,4H), 3.21(t,2H),                                                                              "                                                      6.20(s,1H), 7.08(s,2H),                                                       and 11.20(br,1H)                                                              0.98(t,3H), 1.16(t,6H),                                                       1.73(six,2H), 2.00(s,3H),                                  129   1655, 1683                                                                            KBr  2.31(s,3H), 2.57(q,4H),                                                                              CDCl.sub.3                                             3.20(t,2H), 6.86(s,2H),                                                       11.00(br,1H), and 2.27(s,3H)                                                  0.98(t,3H), 1.17(t,6H),                                                       1.75(six,2H), 2.33(s,3H),                                  130                2.27(s,3H), 2.57(q,4H),                                                                              "                                                      3.20(t,2H), 6.22(s,1H),                                                       11.03(br,1H), and 6.87(s,2H)                               131                                                                           132                                                                                              0.99(t,3H), 1.19(t,6H),                                                       1.73(six,2H), 2.02(s,3H),                                  133   1655, 1680,                                                                           neat 2.36(s,3H), 2.63(q,4H),                                                                              CDCl.sub.3                                2230         3.19(t,2H), 7.34(s,2H),                                                       and 11.57(br,1H)                                                              1.00(t,3H), 1.16(t,6H),                                                       1.73(six,2H), 2.32(s,3H),                                  134   1640, 1660,                                                                           KBr  2.63(q,4H), 3.21(t,2H),                                                                              CDCl.sub.3                                1685, 2230   6.27(s,1H), 7.36(s,2H),                                                       and 11.35(br.1H)                                           135   1647, 1655,                                                                   1675    KBr                                                                                0.95(t,3H), 1.13(t,6H),                                                       1.40-2.00(m,6H),                                           136   1657, 1675                                                                            "    2.35-2.55(m,4H),       CDCl.sub.3                                             2.52(q,4H), 3.19(t,2H),                                                       7.15(s,2H), and 11.22(br,1H)                                                  0.96(t,3H), 1.40-3.00(m,8H),                                                  2.55(q,4H), 3.18(t,2H),                                    137                7.17(s,2H), 11.08(br,1H),                                                                            "                                                      and 1.14(t,6H)                                             __________________________________________________________________________

                  TABLE 3                                                         ______________________________________                                                 Evaluation                                                                      Conc. Plants                                                                  (ppm) X          Y     Z                                           ______________________________________                                        Compound                                                                      No.                                                                           1            20      1          1   1                                                      100     5          4   3                                         2            20      1          2   1                                                      100     5          5   4                                         3            20      5          5   5                                                      100     5          5   5                                         6            20      2          5   1                                                      100     5          5   3                                         7            20      1          2   1                                                      100     4          5   2                                         8            20      2          5   1                                                      100     5          5   3                                         10           20      1          2   3                                                      100     3          2   3                                         11           20      2          2   3                                                      100     2          5   4                                         13           20      5          5   5                                                      100     5          5   5                                         14           20      1          1   4                                                      100     1          3   5                                         15           20      5          5   5                                                      100     5          5   5                                         16           20      5          5   5                                                      100     5          5   5                                         18           20      2          1   1                                                      100     3          4   2                                         19           20      1          2   1                                                      100     4          3   1                                         20           20      4          4   3                                                      100     5          5   5                                         21           20      1          4   4                                                      100     5          5   5                                         23           20      5          5   3                                                      100     5          5   5                                         24           20      5          5   5                                                      100     5          5   5                                         25           20      4          4   3                                                      100     4          5   4                                         26           20      4          5   5                                                      100     5          5   5                                         27           20      3          5   5                                                      100     5          5   5                                         28           20      5          5   5                                                      100     5          5   5                                         29           20      5          5   5                                                      100     5          5   5                                         30           20      3          5   5                                                      100     5          5   5                                         31           20      4          5   5                                                      100     5          5   5                                         32           20      5          5   5                                                      100     5          5   5                                         33           20      5          5   5                                                      100     5          5   5                                         37           20      5          5   4                                                      100     5          5   5                                         39           20      1          2   4                                                      100     4          4   5                                         40           20      1          4   5                                                      100     1          4   5                                         41           20      2          4   5                                                      100     5          4   5                                         42           20      5          5   5                                                      100     5          5   5                                         43           20      5          5   5                                                      100     5          5   5                                         44           20      4          5   4                                                      100     4          5   5                                         47           20      5          5   5                                                      100     5          5   5                                         48           20      2          2   2                                                      100     4          3   5                                         50           20      2          2   2                                                      100     2          3   3                                         51           20      5          5   5                                                      100     5          5   5                                         56           20      1          1   1                                                      100     2          5   2                                         58           20      1          1   2                                                      100     3          3   4                                         59           20      4          4   5                                                      100     5          5   5                                         60           20      1          2   3                                                      100     2          4   3                                         61           20      3          3   1                                                      100     3          4   3                                         62           20      1          3   2                                                      100     2          3   2                                         63           20      1          1   2                                                      100     2          3   3                                         64           20      2          5   5                                                      100     5          5   5                                         65           20      5          5   5                                                      100     5          5   5                                         66           20      5          5   5                                                      100     5          5   5                                         69           20      1          4   3                                                      100     2          4   3                                         70           20      5          5   5                                                      100     5          5   5                                         71           20      5          5   5                                                      100     5          5   5                                         72           20      4          5   3                                                      100     5          5   5                                         73           20      5          5   5                                                      100     5          5   5                                         74           20      4          5   5                                                      100     5          5   5                                         75           20      5          5   5                                                      100     5          5   5                                         76           20      5          5   5                                                      100     5          5   5                                         77           20      2          5   5                                                      100     2          5   5                                         78           20      1          3   3                                                      100     2          3   3                                         79           20      1          3   2                                                      100     2          3   2                                         81           20      1          2   4                                                      100     2          2   5                                         85           20      2          4   5                                                      100     2          5   5                                         86           20      5          5   5                                                      100     5          5   5                                         87           20      5          5   5                                                      100     5          5   5                                         88           20      5          5   5                                                      100     5          5   5                                         89           20      5          5   5                                                      100     5          5   5                                         90           20      2          4   4                                                      100     2          4   4                                         91           20      5          5   2                                                      100     5          5   3                                         92           20      4          5   3                                                      100     4          5   3                                         93           20      2          3   2                                                      100     3          4   2                                         94           20      5          5   5                                                      100     5          5   5                                         95           20      4          4   5                                                      100     5          5   5                                         96           20      3          3   4                                                      100     4          4   5                                         97           20      4          5   5                                                      100     5          5   5                                         98           20      5          5   4                                                      100     5          5   5                                         99           20      5          5   3                                                      100     5          5   4                                         100          20      4          4   4                                                      100     5          5   5                                         101          20      4          5   3                                                      100     5          5   4                                         102          20      4          4   4                                                      100     5          5   5                                         103          20      4          4   4                                                      100     5          5   5                                         104          20      4          4   4                                                      100     5          5   5                                         105          20      5          5   5                                                      100     5          5   5                                         106          20      4          5   4                                                      100     5          5   4                                         107          20      4          5   5                                                      100     5          5   5                                         108          20      4          5   5                                                      100     5          5   5                                         109          20      4          5   5                                                      100     5          5   5                                         110          20      3          3   4                                                      100     3          3   4                                         111          20      4          5   4                                                      100     5          5   5                                         112          20      4          5   5                                                      100     5          5   5                                         113          20      1          3   2                                                      100     2          4   3                                         114          20      2          3   2                                                      100     3          4   3                                         115          20      1          1   1                                                      100     2          3   2                                         118          20      4          5   2                                                      100     5          5   3                                         119          20      4          5   4                                                      100     5          5   5                                         120          20      2          4   1                                                      100     3          4   2                                         121          20      3          3   1                                                      100     3          3   2                                         122          20      2          4   5                                                      100     2          5   5                                         123          20      3          5   5                                                      100     5          5   5                                         124          20      5          5   5                                                      100     5          5   5                                         125          20      4          5   5                                                      100     5          5   5                                         126          20      1          1   1                                                      100     2          2   2                                         127          20      5          5   5                                                      100     5          5   5                                         128          20      5          5   5                                                      100     5          5   5                                         129          20      5          5   5                                                      100     5          5   5                                         130          20      5          5   5                                                      100     5          5   5                                         131          20      5          5   5                                                      100     5          5   5                                         132          20      5          5   5                                                      100     5          5   5                                         133          20      5          5   5                                                      100     5          5   5                                         134          20      5          5   5                                                      100     5          5   5                                         135          20      5          5   5                                                      100     5          5   5                                         136          20      4          5   2                                                      100     5          5   5                                         137          20      5          5   5                                                      100     5          5   5                                         138          20      5          5   5                                                      100     5          5   5                                         139          20      5          5   5                                                      100     5          5   5                                         Reference                                                                     Compound                                                                      No.                                                                           1            20      1          1   1                                                      100     1          1   1                                         2            20      1          1   1                                                      100     1          1   1                                         3            20      1          1   1                                                      100     1          1   1                                         ______________________________________                                         X: Oryza sativa L.                                                            Y: Echinochloa crus-galli L.                                                  Z: Raphanus sativus L.                                                        (note)                                                                        Reference compound No. 1:                                                     2,6dimethyl-4-oxo-N--phenyl-4H--pyran-3-carboxamide,                          Reference compound No. 2:                                                     2,6dimethyl-N--(3-nitrophenyl)-4-oxo-4H--pyran-3-carboxamide,                 Reference compound No. 3: 4oxo-N,2,6-triphenyl-4H--pyran-3-carboxamide.  

It is clear from Table 3 that known compounds (Reference compound Nos.1-3) have no plant-growth regulating activity, while the compounds ofthis invention have remarkable plant-growth regulating activity.

What we claim is:
 1. A compound of the formula (I) ##STR11## wherein: R₁is a C₂₋₁₁ alkyl, a lower alkenyl, a lower alkynyl, a cycloalkyl, alower alkoxyalkyl, a lower haloalkyl, an aralkyl selected from the groupconsisting of benzyl, 3-phenylpropyl and 4-phenylbutyl; or a substitutedaralkyl selected from the group consisting of benzyl, 3-phenylpropyl and4-phenylbutyl, wherein the phenyl group is substituted by halogen, loweralkyl, lower alkoxy, or cyano; or phenyl; or a phenyl substituted byhalogen, lower alkyl, lower alkoxy, nitro or cyano;R₂, R₃ and R₄ are thesame or different, and each is hydrogen, a halogen, cyano, nitro, amino,a lower alkyl, a lower haloalkyl, hydroxy, a lower alkoxy, an phenyloxy,naphthyloxy, carboxy or a lower alkoxycarbonyl; R₅ and R₆ are combinedto form a group of --(CH₂)_(m) --, wherein m is 3 or
 4. 2. A compound ofclaim 1 wherein ##STR12## in the formula (I) is phenyl.
 3. A compound ofclaim 1 wherein ##STR13## in the formula (I) is4-bromo-2,6-diethylphenyl, 4-chloro-2,6-diethylphenyl, 2,6-diethylphenylor 2,3-dimethylphenyl.
 4. A compound of claim 1 wherein R₁ in theformula (I) is an alkyl, lower alkenyl or lower alkynyl group having 2to 5 carbon atoms.
 5. A compound of claim 1 wherein R₁ in the formula(I) is 3-trifluoromethylphenyl, 3-chlorophenyl, 3-bromophenyl,3-nitrophenyl or 3-cyanophenyl.
 6. A compound of claim 1 selected fromthe group consistingof:N-(4-bromo-2,6-diethylphenyl)-2-butyl-5,6,7,8-tetrahydro-4-oxo-4H-benzopyran-3-carboxamide,2-butyl-N-(2,6-diethylphenyl)-4,5,6,7-tetrahydro-4-oxo-cyclopenta[b]pyran-3-carboxamide,N-(2,6-diethylphenyl)-4,5,6,7-tetrahydro-4-oxo-2-propyl-cyclopenta[b]pyran-3-carboxamide,andN-(4-bromo-2,6-diethylphenyl)-2-butyl-4,5,6,7-tetrahydro-4-oxo-cyclopenta[b]pyran-3-carboxamide.7. A herbicidal composition comprising an inert carrier or solvent and aherbicidally effective amount of a compound of formula I: ##STR14##wherein: R₁ is a C₂₋₁₁ alkyl, a lower alkenyl, a lower alkynyl, acycloalkyl, a lower alkoxyalkyl, a lower haloalkyl, an aralkyl selectedfrom the group consisting of benzyl, 3-phenylpropyl and 4-phenylbutyl;or a substituted aralkyl selected from the group consisting of benzyl,3-phenylpropyl and 4-phenylbutyl, wherein the phenyl group issubstituted by halogen, lower alkyl, lower alkoxy, or cyano; or phenyl;or a phenyl substituted by halogen, lower alkyl, lower alkoxy, nitro orcyano;R₂, R₃ and R₄ are the same or different, and each is hydrogen, ahalogen, cyano, nitro, amino, a lower alkyl, a lower haloalkyl, hydroxy,a lower alkoxy, an phenyloxy, naphthyloxy, carboxy or a loweralkoxycarbonyl; R₅ and R₆ are combined to form a group of --(CH₂)_(m)--, wherein m is 3 or
 4. 8. A herbicidal composition of claim 7, whereinsaid compound of formula I is selected from the group consistingof:N-(4-bromo-2,6-diethylphenyl)-2-butyl-5,6,7,8-tetrahydro-4-oxo-4H-benzopyran-3-carboxamide,2-butyl-N-(2,6-diethylphenyl)-4,5,6,7-tetrahydro-4-oxo-cyclopenta[b]pyran-3-carboxamide,N-(2,6-diethylphenyl)-4,5,6,7-tetrahydro-4-oxo-2-propyl-cyclopenta[b]pyran-3-carboxamide,andN-(4-bromo-2,6-diethylphenyl)-2-butyl-4,5,6,7-tetrahydro-4-oxo-cyclopenta[b]pyran-3-carboxamide.